Triethylamine → 4-[4-Chloro-3-(2,4-dimethoxybenzylsulfamoyl)-phenyl]-3-methyl-2-methylimino-1,3-thiazolidine-4-ol-hydrochloride

HRID 461187Notes

Reaction equation

HRID 461187 reaction equation
Br.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:17])[CH2:13][S:12][C:11](=[N:14][CH3:15])[N:10]2[CH3:16])=[CH:5][C:4]=1[S:18](Cl)(=[O:20])=[O:19].C(N(CC)CC)C.[CH3:29][O:30][C:31]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:32]=1[CH2:33][NH2:34]>O>[ClH:2].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([OH:17])[CH2:13][S:12][C:11](=[N:14][CH3:15])[N:10]2[CH3:16])=[CH:5][C:4]=1[S:18](=[O:20])(=[O:19])[NH:34][CH2:33][C:32]1[CH:35]=[CH:36][C:37]([O:39][CH3:40])=[CH:38][C:31]=1[O:30][CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5972502,4-DimethoxybenzylamineHCID 227604894-Chloro-3-chlorosulfonylphenyl-3-methyl-2-methylimino-1,3-thiazolidine-4-ol-hydrobromide

Product 1

HCID 227604194-[4-Chloro-3-(2,4-dimethoxybenzylsulfamoyl)-phenyl]-3-methyl-2-methylimino-1,3-thiazolidine-4-ol-hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.8 g of 4-(4-chloro-3-chlorosulfonylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ol-hydrobromide were reacted as prescribed in Example 76 with 5 g of triethyl amine and 3.5 g of 2,4-dimethoxybenzyl amine and worked up. After treating with water, the amorphous 4-[4-chloro-3-(2,4-di-methoxybenzylsulfamoyl)-phenyl]-3-methyl-2-methylimino-1,3-thiazolidine-4-ol was extracted with 70 ml of ethyl acetate, dried over sodium sulfate and the solvent was acidified with ethanolic hydrochloric acid (15%). The amorphous precipitate end product was crystallized under isopropanol. Melting point: 163° C (decomposition).

Workup

  1. extractionthe amorphous 4-[4-chloro-3-(2,4-di-methoxybenzylsulfamoyl)-phenyl]-3-methyl-2-methylimino-1,3-thiazolidine-4-ol was extracted with 70 ml of ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe amorphous precipitate end product was crystallized under isopropanol

Sources & evidence

ORD record
ord-e0f110ab932d4ec8b2faec9f46b1793e
Source dataset
uspto-grants-1977_12
Patent number
US04061761

Reaction notes

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