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CAS 14034-59-4
Ethane-1,2-diamine 4-methylbenzenesulfonate
Codes: Xylometazoline Hydrochloride-007, Oxymetazoline Hydrochloride-008
Application context (from source-drug indications)
AnaesthesiaOxymetazoline Hydrochloride/Tetracaine HydrochloridePeriapical periodontitisOxymetazoline Hydrochloride/Tetracaine HydrochlorideDental cariesOxymetazoline Hydrochloride/Tetracaine HydrochlorideNasal congestionXylometazoline HydrochlorideRhinitisXylometazoline HydrochlorideCommon coldXylometazoline HydrochlorideNasal congestionOxymetazoline HydrochlorideCongestionOxymetazoline HydrochloridePtosisOxymetazoline HydrochlorideFunctional faecal incontinenceOxymetazoline HydrochlorideRosaceaOxymetazoline HydrochlorideRashOxymetazoline Hydrochloride
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Dexpanthenol/Xylometazoline Hydrochloride | Tier C — Watch / trade | - |
| Oxymetazoline Hydrochloride/Tetracaine Hydrochloride | Tier C — Watch / trade | - |
| Xylometazoline Hydrochloride | Tier C — Watch / trade | - |
| Oxymetazoline Hydrochloride | Tier C — Watch / trade | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
Dexpanthenol/Xylometazoline HydrochlorideOptimised routesteps: 5total yield: 12.4g(Xylometazoline Hydrochloride (API))
1,3-Dimethylbenzene→1,1-Dimethylethanol→1-tert-Butyl-3,5-dimethylbenzene→1-Chloro-1-methoxymethane→5-tert-Butyl-2-(chloromethyl)-1,3-dimethylbenzene→(4-tert-Butyl-2,6-dimethylphenyl)acetonitrile→Ethane-1,2-diamine 4-methylbenzenesulfonate→2-(4-tert-Butyl-2,6-dimethylbenzyl)-4,5-dihydro-1H-imidazole 4-methylbenzenesulfonate
Oxymetazoline Hydrochloride/Tetracaine HydrochlorideOptimised routesteps: 5total yield: 7.5g(Oxymetazoline hydrochloride (API))
4-tert-Butyl-2,6-dimethylbenzene-1,3-diol→1-Chloro-1-methoxymethane→6-tert-Butyl-3-(chloromethyl)-2,4-dimethylphenol→(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetonitrile→4,5-Dihydro-1H-imidazole-2-thiol→6-tert-Butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol→2-(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetamide→Ethane-1,2-diamine 4-methylbenzenesulfonate→Ethane-1,2-diamine hydrobromide
Oxymetazoline Hydrochloride/Tetracaine HydrochlorideOptimised routesteps: 6total yield: 26g(Oxymetazoline hydrochloride (API))
(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetonitrile→Ethane-1,2-diamine→N-[2-(Acetamido)ethyl]acetamide→6-tert-Butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol→(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetyl chloride→(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetic acid→Ethane-1,2-diamine 4-methylbenzenesulfonate→2-(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetamide→2-Bromoethanamine hydrobromide→Ethylene dibromide→Ethyl 2-(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)ethanimidoate hydrochloride
Xylometazoline HydrochlorideOptimised routesteps: 5total yield: 12.4g(Xylometazoline Hydrochloride (API))
1,3-Dimethylbenzene→1,1-Dimethylethanol→1-tert-Butyl-3,5-dimethylbenzene→1-Chloro-1-methoxymethane→5-tert-Butyl-2-(chloromethyl)-1,3-dimethylbenzene→(4-tert-Butyl-2,6-dimethylphenyl)acetonitrile→Ethane-1,2-diamine 4-methylbenzenesulfonate→2-(4-tert-Butyl-2,6-dimethylbenzyl)-4,5-dihydro-1H-imidazole 4-methylbenzenesulfonate
Oxymetazoline HydrochlorideOptimised routesteps: 5total yield: 7.5g(Oxymetazoline hydrochloride (API))
4-tert-Butyl-2,6-dimethylbenzene-1,3-diol→1-Chloro-1-methoxymethane→6-tert-Butyl-3-(chloromethyl)-2,4-dimethylphenol→(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetonitrile→4,5-Dihydro-1H-imidazole-2-thiol→6-tert-Butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol→2-(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetamide→Ethane-1,2-diamine 4-methylbenzenesulfonate→Ethane-1,2-diamine hydrobromide
Oxymetazoline HydrochlorideOptimised routesteps: 6total yield: 26g(Oxymetazoline hydrochloride (API))
(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetonitrile→Ethane-1,2-diamine→N-[2-(Acetamido)ethyl]acetamide→6-tert-Butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol→(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetyl chloride→(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetic acid→Ethane-1,2-diamine 4-methylbenzenesulfonate→2-(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetamide→2-Bromoethanamine hydrobromide→Ethylene dibromide→Ethyl 2-(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)ethanimidoate hydrochloride
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