Dimethylformamide → 3-[(5-Chloro-1,3-benzodithiol-2-ylidene)amino]-2-thioxo-4-thiazolidinone

HRID 2419140Notes

Reaction equation

HRID 2419140 reaction equation
[I-].[Cl:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][C:8](=[N+:10](C)C3C=CC=CC=3)[S:9][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].N[N:27]1[C:31](=[O:32])[CH2:30][S:29][C:28]1=[S:33].CN(C)C=O>O>[Cl:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][C:8](=[N:10][N:27]3[C:31](=[O:32])[CH2:30][S:29][C:28]3=[S:33])[S:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 740333-AminorhodanineHCID 203138445-Chloro-N-methyl-N-phenyl-1,3-benzodithiol-2-iminium iodide

Product 1

HCID 736760723-[(5-Chloro-1,3-benzodithiol-2-ylidene)amino]-2-thioxo-4-thiazolidinoneYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of the methiodide of 5-chloro-N-methyl-N-phenyl-1,3-benzodithiol-2-iminium iodide (1.9 g), sodium carbonate (121 mg), N-aminorhodanine (338 mg) and dimethylformamide (20 ml) is heated at 50° C for 3 hours. The mixture is poured into water and the precipitate which forms is filtered and washed with water. The product is recrystallized from dimethylformamide to yield 600 mg of the title compound, melting point 312°-314° C.

Workup

  1. filtrationthe precipitate which forms is filtered
  2. washwashed with water
  3. customThe product is recrystallized from dimethylformamide

Sources & evidence

ORD record
ord-e3e871ef7ecb4fb68e413882d542ce55
Source dataset
uspto-grants-1978_08
Patent number
US04104467

Reaction notes

Loading…