4-Chloroaniline → 4'-Chloro-2-(2,2-difluorocyclopropyl)acetanilide

HRID 703523Notes

Reaction equation

HRID 703523 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[F:25][C:26]1([F:33])[CH2:28][CH:27]1[CH2:29][C:30](Cl)=[O:31]>O1CCCC1.O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:30](=[O:31])[CH2:29][CH:27]2[CH2:28][C:26]2([F:33])[F:25])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 144585042-(2,2-Difluorocyclopropyl)acetyl chloride

Product 1

HCID 144585054'-Chloro-2-(2,2-difluorocyclopropyl)acetanilide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

15.3 g (120 mmol) 4-Chloroaniline, 18.4 ml (132 mmol) triethylamine and 50 mg dimethylaminopyridine dissolved in 150 ml tetrahydrofuran was treated, under ice-cooling, with 18.6 g (120 mmol) 2-(2,2-difluorocyclopropyl)acetyl chloride. The mixture was stirred for 2 hours at room temperature and poured into 1000 ml water. The precipitated crystals were separated, washed with a small amount of hydrochloric acid and dried in vacuo (200 mbar). A sample was analysed by thin layer chromatography (dichloromethane:methanol=95:5) (Rf=0.62).

Workup

  1. additionwas treated, under ice-
  2. customThe precipitated crystals were separated
  3. washwashed with a small amount of hydrochloric acid
  4. customdried in vacuo (200 mbar)

Sources & evidence

ORD record
ord-ac868c99b45d4bf0bff9fac65b8d2257
Source dataset
uspto-grants-1991_01
Patent number
US04983630

Reaction notes

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