Hydrochloric Acid → HCID 59556306, compound

HRID 1172664Notes

Reaction equation

HRID 1172664 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[S:5][C:6]=1[CH:7]=[O:8].Br[C:20]([F:24])([F:23])[CH:21]=[CH2:22].Cl>CN(C)C=O>[F:23][C:20]([F:24])([CH:21]=[CH2:22])[CH:7]([C:6]1[S:5][C:4]([C:9]2[CH:10]=[CH:11][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:14]=2)=[N:3][C:2]=1[CH3:1])[OH:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5550853-bromo-3,3-difluoroprop-1-eneHCID 27828994-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde

Product 1

HCID 59556306HCID 59556306, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.0 g 4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbaldehyde and 868 mg 3-bromo-3,3-difluorpropene in 10 ml dimethylformamide 425 mg Indium were added and the resulting suspension was stirred in an ultrasonic bath for two hours. Then 20 ml 1 N hydrochloric acid were added and the mixture stirred at room temperature for thirty minutes. The mixture was extracted three times with portions of 50 ml ethyl acetate. The combined organic layers were dried over MgSO4. The solvent was evaporated in vacuo. The resulting residue was purified by reversed phase HPLC to obtain 740 mg 2,2-Difluoro-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-but-3-en-1-ol as a colorless lyophilisate.

Workup

  1. stirringthe mixture stirred at room temperature for thirty minutes
  2. extractionThe mixture was extracted three times with portions of 50 ml ethyl acetate
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customThe solvent was evaporated in vacuo
  5. customThe resulting residue was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-51237ab247af471281c0608f9fa68260
Source dataset
uspto-grants-2010_11
Patent number
US07834030B2

Reaction notes

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