4-(Trifluoromethyl)benzoyl chloride → HCID 8643478, compound

HRID 445291Notes

Reaction equation

HRID 445291 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][NH2:6].C(N(C(C)C)CC)(C)C.[F:20][C:21]([F:32])([F:31])[C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>ClCCl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][NH:6][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:22]([C:21]([F:20])([F:31])[F:32])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 81531DiisopropylethylamineHCID 6433572-(2-Fluorophenyl)ethylamine

Product 1

HCID 8643478HCID 8643478, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 250-mL, round-bottomed flask containing a solution of 2-fluorophenethylamine (4.7 mL, 35.9 mmol) and diisopropylethylamine (6.3 mL, 35.9 mmol) in dichloromethane (35 mL) was cooled to 0° C. and treated dropwise with 4-(trifluoromethyl)benzoyl chloride (5.4 mL, 35.9 mmol) over 5 min. The ice-bath was removed after 2 h and the reaction mixture was stirred overnight. The precipitate formed was collected by filtration. The filtrate was diluted with dichloromethane (100 mL) and transferred to a separatory funnel, extracted with water (35 mL), brine (25 mL), and 1N HCl (25 mL). The dichloromethane layer was separated and formation of more precipitate was observed which was collected by filtration. The solids collected were combined and dried under vacuum to yield N-(2-fluorophenethyl)-4-(trifluoromethyl)benzamide as an off-white solid. MS (ESI pos. ion) m/z: 312 (M+H).

Workup

  1. customThe ice-bath was removed after 2 h
  2. customThe precipitate formed
  3. filtrationwas collected by filtration
  4. additionThe filtrate was diluted with dichloromethane (100 mL)
  5. customtransferred to a separatory funnel
  6. extractionextracted with water (35 mL), brine (25 mL), and 1N HCl (25 mL)
  7. customThe dichloromethane layer was separated
  8. filtrationwas collected by filtration
  9. customThe solids collected
  10. customdried under vacuum

Sources & evidence

ORD record
ord-d8f1564b1d75466cbbe5be3b6e584557
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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