Dimethylformamide → 2-Difluoroacetylimino-3(3-trifluoromethylphenyl)-5-methylthiazoline

HRID 375386Notes

Reaction equation

HRID 375386 reaction equation
[NH:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH:5]=[C:4]([CH3:17])[S:3]1.C(NCC)C.C(N(CC)CC)C.[F:30][C:31]([F:35])=[C:32](F)F.CN(C)C=[O:39]>>[F:30][CH:31]([F:35])[C:32]([N:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:14])[F:15])[CH:8]=2)[CH:5]=[C:4]([CH3:17])[S:3]1)=[O:39]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8021DiethylamineHCID 8301TetrafluoroethyleneHCID 8471TriethylamineHCID 110215462(3H)-Thiazolimine, 5-methyl-3-[3-(trifluoromethyl)phenyl]-

Product 1

HCID 110889832-Difluoroacetylimino-3(3-trifluoromethylphenyl)-5-methylthiazolineYield 65%

Procedure

A solution of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (0.52 g, 2.0 mmol), diethylamine (0.44 g, 6.0 mmol), triethylamine (0.61 g, 6.0 mmol) in N,N-dimethylformamide (10 ml) charged in a reaction flask was reacted with tetrafluoroethylene in the flask atmosphere (0.70 g, 7.0 mmol), which was supplied from a balloon tothe flask, at 50° C. for 21 hours. After cooling to an ambient temperature, the reaction mixture was poured into ice-water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and then brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was subjected to silica gel column chromatography, which afforded 2-difluoroacetylimino-3(3-trifluoromethylphenyl)-5-methylthiazoline (0.44 g, 1.3 mmol, yield 65%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialbrine, and dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-eab9f5699d8545f7aaed6d0e26a88c89
Source dataset
uspto-grants-1996_01
Patent number
US05484933

Reaction notes

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