Triethylamine → 4-(4-Chloro-3-cyclopentylmethylsulfamoylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ol

HRID 461174Notes

Reaction equation

HRID 461174 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].[CH:22]1([CH2:27][NH2:28])[CH2:26][CH2:25][CH2:24][CH2:23]1.C(N(CC)CC)C>C(O)C>[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:28][CH2:27][CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 80153CyclopentanemethylamineHCID 227604894-Chloro-3-chlorosulfonylphenyl-3-methyl-2-methylimino-1,3-thiazolidine-4-ol-hydrobromide

Product 1

HCID 227604914-(4-Chloro-3-cyclopentylmethylsulfamoylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8.8 g of 4-(4-chloro-3-chlorosulfonylphenyl)-3-methyl-2-methylimino-1,3-thiazolidine-4-ol-hydrobromide were introduced portionswise at 20° C in a stirred mixture of 4 g of cyclopentylmethyl amine, 8 g of triethyl amine and 100 ml of ethanol and the reaction mixture was allowed to stand over night. The solvent was distilled off under reduced pressure and the amorphous end product was crystallized under 80 ml of water. Colorless solid body, decomposition beginning at 80° C, γ C=N 1620 cm-1.

Workup

  1. waitto stand over night
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe amorphous end product was crystallized under 80 ml of water
  4. customat 80° C

Sources & evidence

ORD record
ord-bd7c202499424e0d9473c27404e7a9e7
Source dataset
uspto-grants-1977_12
Patent number
US04061761

Reaction notes

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