Water → HCID 8023087, compound

HRID 1883684Notes

Reaction equation

HRID 1883684 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1.C(N(CC)CC)C.O>ClC(Cl)C>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:19][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 754524-MethoxybenzylamineHCID 801724-Cyanobenzoyl chloride

Product 1

HCID 8023087HCID 8023087, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

825 mg of 4-cyanobenzoyl chloride was dissolved in 9 ml of dichloroethane, and mixed with 0.69 ml of 4-methoxybenzylamine and 1.57 ml of triethylamine, followed by stirring for 2.5 hours. Thereafter, the reaction was stopped by the addition of 1 ml of distilled water. After the product was extracted with chloroform, the extract was successively washed with 2 N hydrochloric acid, a saturated aqueous solution of sodium hydrogen carbonate, and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. After the solvent was distilled off, the resulting crude product was purified by silica gel column chromatography (using a 20:1 mixture of chloroform and acetone as the eluent) to obtain 1.29 g of 4-cyano-N-(4-methoxy-benzyl)benzamide.

Workup

  1. extractionAfter the product was extracted with chloroform
  2. washthe extract was successively washed with 2 N hydrochloric acid
  3. dry with materiala saturated aqueous solution of sodium hydrogen carbonate, and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  4. distillationAfter the solvent was distilled off
  5. customthe resulting crude product was purified by silica gel column chromatography (
  6. additiona 20:1 mixture of chloroform and acetone as the eluent)

Sources & evidence

ORD record
ord-72a5b61b792e453688b1506a4506fd01
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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