Water → N-[2,6-Dimethyl-4-(4-trifluoromethyl-benzylamino)-phenyl]-acetamide

HRID 1820147Notes

Reaction equation

HRID 1820147 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10](=[O:12])[CH3:11])=[C:4]([CH3:13])[CH:3]=1.[F:14][C:15]([F:25])([F:24])[C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.O>C(O)C>[CH3:8][C:6]1[CH:7]=[C:2]([NH:1][CH2:20][C:19]2[CH:18]=[CH:17][C:16]([C:15]([F:14])([F:24])[F:25])=[CH:23][CH:22]=2)[CH:3]=[C:4]([CH3:13])[C:5]=1[NH:9][C:10](=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 679964-(Trifluoromethyl)benzaldehydeHCID 11959019N-(4-Amino-2,6-dimethylphenyl)acetamide

Product 1

HCID 11652937N-[2,6-Dimethyl-4-(4-trifluoromethyl-benzylamino)-phenyl]-acetamideYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(4-Amino-2,6-dimethyl-phenyl)-acetamide (1.2 g) and 4-trifluoromethyl-benzaldehyde (1.3 g) were dissolved in ethanol (100 mL) and refluxed for 16 h. The reaction mixture was poured into water (3 L) and the precipitate collected by filtration. Sodium cyanoborohydride (2 g) and acetic acid (2 mL) were added to the precipitate dispersed in methanol (50 mL) and stirred for 15 minutes. The reaction mixture was filtered, water (100 mL) was added and the organic solvent was removed in vacuo. The product was allowed to precipitate at 25° C. and collected by filtration and washed with water (200 mL) to furnish 0.68 g (30% yield) of the title compound as a pale yellow solid. LC-MS (m/z) 337 (MH+); tR=2.39, (UV, ELSD) 99%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.95 (s, 3H), 1.96 (s, 6H), 4.34 (d, 2H), 6.18 (t, 1H), 6.25 (s, 2H), 7.55 (d, 2H), 7.69 (d, 2H), 8.81 (s, 1H).

Workup

  1. temperaturerefluxed for 16 h
  2. filtrationthe precipitate collected by filtration
  3. additionSodium cyanoborohydride (2 g) and acetic acid (2 mL) were added to the precipitate
  4. additiondispersed in methanol (50 mL)
  5. filtrationThe reaction mixture was filtered
  6. additionwater (100 mL) was added
  7. customthe organic solvent was removed in vacuo
  8. customto precipitate at 25° C.
  9. filtrationcollected by filtration
  10. washwashed with water (200 mL)

Sources & evidence

ORD record
ord-cae11be3445e47e8aac80deab99fa961
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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