4-(Trifluoromethyl)phenyl isocyanate → HCID 18537594, compound

HRID 412353Notes

Reaction equation

HRID 412353 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.[F:37][C:38]([F:49])([F:48])[C:39]1[CH:44]=[CH:43][C:42]([N:45]=[C:46]=[O:47])=[CH:41][CH:40]=1>CN(C)C=O>[O:31]=[C:29]1[NH:28][C:27](=[O:32])[CH:26]([CH2:25][C:24]2[CH:33]=[CH:34][C:21]([O:20][CH2:19][C:17]3[N:16]([CH3:35])[C:15]4[CH:36]=[C:11]([O:10][CH2:9][CH2:8][C:5]5[CH:6]=[CH:7][C:2]([NH:1][C:46]([NH:45][C:42]6[CH:41]=[CH:40][C:39]([C:38]([F:37])([F:48])[F:49])=[CH:44][CH:43]=6)=[O:47])=[CH:3][CH:4]=5)[CH:12]=[CH:13][C:14]=4[N:18]=3)=[CH:22][CH:23]=2)[S:30]1

Participants

4

Reactant 2

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 86587775HCID 86587775, compound

Product 1

HCID 18537594HCID 18537594, compoundYield 72.9%

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 α,α,α-trifluoro-p-tolyl isocyanate (0.17 g) and the mixture was stirred at room temperature for 2 hours 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 a mixture of ethyl acetate and diethyl ether (1:1). The precipitate was isolated by filtration and washed with diethyl ether to afford the title compound (0.4 g, mp 145-147° 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
  7. additiona mixture of ethyl acetate and diethyl ether (1:1)
  8. customThe precipitate was isolated by filtration
  9. washwashed with diethyl ether

Sources & evidence

ORD record
ord-2ef920e5a3d141dbad8492e472ca4621
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

Loading…