Aniline, N-(2,2,2-trifluoroethyl)- → HCID 58117491, compound

HRID 1640235

Reaction equation

HRID 1640235 reaction equation
[F:1][C:2]([F:12])([F:11])[CH2:3][NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+].[Cl:15][C:16]1[N:21]=[CH:20][N:19]=[C:18]([C:22](Cl)=[O:23])[CH:17]=1.C(=O)([O-])O.[Na+]>ClCCl.C(O)C>[Cl:15][C:16]1[N:21]=[CH:20][N:19]=[C:18]([C:22]([N:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:3][C:2]([F:11])([F:12])[F:1])=[O:23])[CH:17]=1

Participants

7

Reactant 4

HCID 9596Aniline, N-(2,2,2-trifluoroethyl)-HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 184220986-Chloropyrimidine-4-carbonyl chloride

Product 1

HCID 58117491HCID 58117491, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

200 mg (1.14 mmol) N-(2,2,2-trifluoroethyl)aniline and 1.14 mL (1.14 mmol) of a 1M sodium hydroxide solution were added dropwise to 212 mg (1.2 mmol) 6-chloropyrimidine-4-carboxylic acid chloride in 20 mL dichloromethane while cooling with a bath of ice and ethanol. The mixture was first stirred for 2 h with cooling and then stirred for 1 h at RT. 50 mL of a saturated sodium hydrogen carbonate solution were added and the mixture was stirred for 10 min. The organic phase was separated off, washed with water and 1M hydrochloric acid, dried on sodium sulphate, filtered and concentrated by rotary evaporation i.vac.

Workup

  1. temperaturewith cooling
  2. stirringstirred for 1 h at RT
  3. stirringthe mixture was stirred for 10 min
  4. customThe organic phase was separated off
  5. washwashed with water and 1M hydrochloric acid
  6. customdried on sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation i.vac

Sources & evidence

ORD record
ord-6c49b08b75a3495792a2a7325fc17df6
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Linked notes

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