3-(Trifluoromethyl)benzoyl chloride → HCID 11345177, compound

HRID 1188694Notes

Reaction equation

HRID 1188694 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].[F:5][C:6]([F:17])([F:16])[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](Cl)=[O:11]>C(Cl)Cl>[CH2:1]([NH:4][C:10](=[O:11])[C:9]1[CH:13]=[CH:14][CH:15]=[C:7]([C:6]([F:5])([F:16])[F:17])[CH:8]=1)[C:2]#[CH:3]

Participants

4

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 239041Propargylamine

Product 1

HCID 11345177HCID 11345177, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-propyn-1-amine (2.0 g, 35.7 mmol) and Hunnig's base (12.5 mL, 71.4 mmol) in CH2Cl2 (20 mL) was added 3-(trifluoromethyl)benzoyl chloride (5.4 mL, 35.7 mmol) at 0° C. The mixture was stirred at rt overnight. CH2Cl2 was added and the organic solution was washed with water twice, brine once, and dried over MgSO4. Concentration and purification by radial chromatography (0-40% EtOAc-hexanes gradient) afforded the title compound (7.0 g, 96% yield): MS (ES) m/z 228 (M+1).

Workup

  1. washthe organic solution was washed with water twice
  2. dry with materialbrine once, and dried over MgSO4
  3. concentrationConcentration and purification by radial chromatography (0-40% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-2633694ac6d0426f8d287e6c3ad0db24
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

Loading…