Benzaldehyde → HCID 178518083, compound

HRID 1987954Notes

Reaction equation

HRID 1987954 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([N+:16]#[C-:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[O-:18][C:19]#[N:20].[K+].[F:22][C:23]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:24]=1[NH2:25].Cl.[NH+]1C=CC=CC=1>CO.O>[CH2:9]([NH:16][C:17]1[CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:25]([C:24]2[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:23]=2[F:22])[C:19](=[O:18])[N:20]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 97092,4-DifluoroanilineHCID 82558Benzyl isocyanideHCID 11378442Potassium cyanateHCID 21584435Pyridinium hydrochloride

Product 1

HCID 178518083HCID 178518083, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2.32 mmol benzaldehyde and 2.32 mmol benzylisocyanide in 1 ml methanol was treated with a solution of 2.32 mmol potassium cyanate in 0.5 ml water. 2.32 mmol of 2,4-difluoroaniline and 2.32 mmol of pyridinium hydrochloride was added and the mixture stirred at room temperature for 48 hours. The solid formed was filtered off and triturated with diethyl ether to give 103 mg of the title compound as a slightly brown solid. Yield=12%. MS (m/e): 378.5 (100%; M+H+), 400.1 (46%; M+Na).

Workup

  1. customThe solid formed
  2. filtrationwas filtered off
  3. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-f7876a78368b463abf187f271e65e27e
Source dataset
uspto-grants-2009_06
Patent number
US07553862B2

Reaction notes

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