Triethylamine → 3-(chloromethyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamide

HRID 1878415Notes

Reaction equation

HRID 1878415 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[F:12][C:13]([F:19])([F:18])[C:14]([CH3:17])([NH2:16])[CH3:15].C(N(CC)CC)C>ClCCl>[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:16][C:14]([CH3:17])([CH3:15])[C:13]([F:19])([F:18])[F:12])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27333243-(Chloromethyl)benzoyl chlorideHCID 112751881,1,1-Trifluoro-2-methylpropan-2-amine

Product 1

HCID 668783493-(chloromethyl)-N-(1,1,1-trifluoro-2-methylpropan-2-yl)benzamideYield 46.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(Chloromethyl)benzoyl chloride (38.5 mmol, 5.48 mL, 7.29 g) was dissolved in dichloromethane (100 mL) and stirred. To this was added a mixture of 1,1,1-trifluoro-2-methylpropan-2-amine (39.3 mmol, 5 g) and triethylamine (59.0 mmol, 8.22 mL, 5.97 g) (dropwise) and stirring continued for 2 hours. The reaction was diluted with dichloromethane and this organic mixture was washed with saturated sodium chloride, water, and saturated sodium chloride. The organic phase was dried with sodium sulfate, filtered and concentrated under vacuum. The residue was purified by silica chromatography (eluting with dichloromethane) to give the title compound (5 g).

Workup

  1. additionTo this was added
  2. stirringstirring
  3. washthis organic mixture was washed with saturated sodium chloride, water, and saturated sodium chloride
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica chromatography (eluting with dichloromethane)

Sources & evidence

ORD record
ord-7e30b201c0bc476a89da9553c9a2d0bf
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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