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

HRID 2102200Notes

Reaction equation

HRID 2102200 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-1ca16b01fd514624a594014e864eefed
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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