Dimethylformamide → 5-cyanomethyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide

HRID 49526

Reaction equation

HRID 49526 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:13][CH3:14])=[C:8]([CH:12]=1)[C:9]([OH:11])=O)#[N:2].CN(C)C=O.[F:20][C:21]([F:31])([F:30])[C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1.C(P(=O)(OCC)OCC)#N>O.C(N(CC)CC)C>[C:1]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:13][CH3:14])=[C:8]([CH:12]=1)[C:9]([NH:27][CH2:26][C:25]1[CH:24]=[CH:23][C:22]([C:21]([F:20])([F:30])[F:31])=[CH:29][CH:28]=1)=[O:11])#[N:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 76257Diethyl cyanophosphonateHCID 768044-(Trifluoromethyl)benzylamineHCID 178305745-Cyanomethyl-2-methoxybenzoic acid

Product 1

HCID 178305785-cyanomethyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To 2.55 g of publicly known 5-cyanomethyl-2-methoxybenzoic acid were added 50 ml of dimethylformamide, 2.57 g of 4-trifluoromethylbenzylamine, 2.66 g of diethyl cyanophosphonate and 2.00 ml of triethylamine, and the mixture was stirred for 20 minutes under cooling with ice and for 6 hours at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. After washed with water, then with saturated brine, the organic layer was dried over anhydrous sodium sulfate. Solvent was distilled off under reduced pressure, and the residue was crystallized from hexane-diethyl ether and collected by filtration to obtain 4.44 g of 5-cyanomethyl-2-methoxy-N-(4-trifluoromethylbenzyl)benzamide as colorless crystals. Melting point 124-125° C. Elemental analysis (%) C16H15F3N2O2 Calcd.(%) C, 62.07; H, 4.34; N, 8.04 Found (%) C, 62.03; H, 4.27; N, 7.99

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter washed with water
  3. dry with materialwith saturated brine, the organic layer was dried over anhydrous sodium sulfate
  4. distillationSolvent was distilled off under reduced pressure
  5. customthe residue was crystallized from hexane-diethyl ether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-15fc2dc155604716b508d487d80a25d1
Source dataset
uspto-grants-2004_03
Patent number
US06706763B1

Linked notes

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