4-Chlorophenyl Isocyanate → HCID 18537671, compound

HRID 412354Notes

Reaction equation

HRID 412354 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]3[N:18]=[C:17]([CH2:19][O:20][C:21]4[CH:34]=[CH:33][C:24]([CH2:25][CH:26]5[S:30][C:29](=[O:31])[NH:28][C:27]5=[O:32])=[CH:23][CH:22]=4)[N:16]([CH3:35])[C:15]=3[CH:36]=2)=[CH:4][CH:3]=1.[Cl:37][C:38]1[CH:43]=[CH:42][C:41]([N:44]=[C:45]=[O:46])=[CH:40][CH:39]=1>CN(C)C=O>[Cl:37][C:38]1[CH:43]=[CH:42][C:41]([NH:44][C:45]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11]3[CH:12]=[CH:13][C:14]4[N:18]=[C:17]([CH2:19][O:20][C:21]5[CH:34]=[CH:33][C:24]([CH2:25][CH:26]6[S:30][C:29](=[O:31])[NH:28][C:27]6=[O:32])=[CH:23][CH:22]=5)[N:16]([CH3:35])[C:15]=4[CH:36]=3)=[CH:4][CH:3]=2)=[O:46])=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 86587775HCID 86587775, compound

Product 1

HCID 18537671HCID 18537671, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-[4-[6-[2-(4-aminophenyl)ethoxy]-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione (0.4 g) and N,N-dimethylformamide (10 ml) was added 4-chlorophenyl isocyanate (0.15 g) and the mixture was stirred at room temperature for 1 hour and allowed to stand overnight. The reaction mixture was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. To the residue was added diethyl ether. The precipitate was isolated by filtration and recrystallized from a mixture of tetrahydrofuran and ethyl acetate to afford the title compound (0.37 g, mp 157-162° C.).

Workup

  1. waitto stand overnight
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. additionTo the residue was added diethyl ether
  7. customThe precipitate was isolated by filtration
  8. customrecrystallized from a mixture of tetrahydrofuran and ethyl acetate

Sources & evidence

ORD record
ord-cb6a5afc5ae74684bc93d7a500b6a117
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

Loading…