4-(Trifluoromethyl)benzoyl chloride → HCID 9051890, compound

HRID 445295Notes

Reaction equation

HRID 445295 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1.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:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][CH2:9][NH:10][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 5339282-(3-Fluorophenyl)ethanamine

Product 1

HCID 9051890HCID 9051890, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 250-mL, round-bottomed flask containing a solution of 2-(3-fluorophenyl)ethanamine (1.3 mL, 9.6 mmol) and diisopropylethylamine (1.7 mL, 9.6 mmol) in dichloromethane (32 mL) was cooled to 0° C. and treated dropwise with 4-(trifluoromethyl)benzoyl chloride (2.0 mL, 9.6 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 and extracted with water (35 mL). The dichloromethane layer was separated and formation of precipitate was observed which was collected by filtration. The filtrate was concentrated to yield more solid and the combined solids were dried under vacuum to yield N-(3-fluorophenethyl)-4-(trifluoromethyl)benzamide as a 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)
  7. customThe dichloromethane layer was separated
  8. filtrationwas collected by filtration
  9. concentrationThe filtrate was concentrated
  10. customto yield more solid
  11. customthe combined solids were dried under vacuum

Sources & evidence

ORD record
ord-610b75128ad947a3b3d632a90f6cb371
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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