3-Benzyl-1-methylthiourea → 2-Benzylimino-4-(4-chloro-3-sulfamoylphenyl)-3-methyl-1,3-thiazolidine-4-ol

HRID 1703870Notes

Reaction equation

HRID 1703870 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([S:12](=[O:15])(=[O:14])[NH2:13])[CH:6]=1)=[O:4].[CH2:16]([NH:23][C:24]([NH:26][CH3:27])=[S:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(OCC)C>[CH2:16]([N:23]=[C:24]1[N:26]([CH3:27])[C:3]([C:5]2[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([S:12](=[O:15])(=[O:14])[NH2:13])[CH:6]=2)([OH:4])[CH2:2][S:25]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 27354893-Benzyl-1-methylthioureaHCID 12952390Bromo-4'-chloro-3'-sulfamoylacetophenone

Product 1

HCID 227605942-Benzylimino-4-(4-chloro-3-sulfamoylphenyl)-3-methyl-1,3-thiazolidine-4-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4.7 g of 2-bromo-4'-chloro-3'-sulfamoylacetophenone and 2.7 g of 1-benzyl-3-methylthiourea were reacted as prescribed in Example 23 and the reaction mixture was introduced into 200 ml of diethyl ether while stirring. The hygroscopic crystals of the 2-benzylimino-4-(4-chloro-3-sulfamoylphenyl)-3-methyl-1,3-thiazolidine-4-ol-hydrobromide were rapidly filtered off, dissolved in 70 ml of water and converted into the end product according to the prescription of Example 28. Colorless solid body: decomposition beginning at 110° C., γC=N 1610 cm-1.

Workup

  1. filtrationThe hygroscopic crystals of the 2-benzylimino-4-(4-chloro-3-sulfamoylphenyl)-3-methyl-1,3-thiazolidine-4-ol-hydrobromide were rapidly filtered off
  2. dissolutiondissolved in 70 ml of water
  3. custombeginning at 110° C.

Sources & evidence

ORD record
ord-2b6112dce3ae49a39122c9e90617151d
Source dataset
uspto-grants-1978_11
Patent number
US04125614

Reaction notes

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