4-Fluoro-3-(trifluoromethyl)benzonitrile → HCID 67364762, compound

HRID 551265Notes

Reaction equation

HRID 551265 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[K].CC(C)([O-])C.Cl.[NH:21]1[CH2:25][CH2:24][C:23](=[O:26])[NH:22]1>CS(C)=O>[N:21]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[C:10]([F:13])([F:12])[F:11])[CH2:25][CH2:24][C:23](=[O:26])[NH:22]1

Participants

5

Reactant 3

HCID 1442554-Fluoro-3-(trifluoromethyl)benzonitrileHCID 27337123-Pyrazolidinone hydrochlorideHCID 50987170Potassium tertbutoxide

Product 1

HCID 67364762HCID 67364762, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

1.00 g (5.29 mmol) 4-fluoro-3-trifluoromethyl-benzonitrile are stirred together with 1.35 g (12.0 mmol) potassium-tert.-butoxide in 4 ml DMSO at ambient temperature under an argon atmosphere for 35 min and then 1.00 g (8.16 mmol) pyrazolidin-3-on-hydrochloride in 3 ml DMSO are added. After stirring at ambient temperature for 68 h the reaction mixture is poured into semisat. sodium chloride solution and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulphate and evaporated down completely i. vac.

Workup

  1. additionis poured into semisat
  2. extractionsodium chloride solution and extracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried over magnesium sulphate
  4. customevaporated down completely

Sources & evidence

ORD record
ord-815a60f10c0147298a35a9ebd38e2039
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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