Water → HCID 57857965, compound

HRID 1675721Notes

Reaction equation

HRID 1675721 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[CH:9][N:10](C)C)=[C:4]([C:13]#[N:14])[CH:3]=1.N[C:16]1[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:17]=1[CH3:23].O>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[N:8]=[CH:9][N:10]=[C:13]2[NH:14][C:18]1[CH:19]=[C:20]([OH:22])[CH:21]=[CH:16][C:17]=1[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 178203-Amino-p-cresolHCID 57857968N'-(4-BroMo-2-cyanophenyl)-N,N-diMethylforMiMidaMide

Product 1

HCID 57857965HCID 57857965, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6.0 g (23.9 mmol) of N′-(4-bromo-2-cyanophenyl)-N,N-dimethylformamidine and 3.24 g (26.3 mmol) of 2-amino-4-hydroxytoluene are suspended in 40 ml of acetic acid and heated under reflux for 1 h. The resulting mixture is cooled and then added to 100 ml of water and extracted with ethyl acetate. The combined organic phases are washed with water and sat. aqueous sodium chloride solution and dried over sodium sulphate, and the solvent is evaporated. 8.0 g (100%) of the desired product are obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 h
  3. temperatureThe resulting mixture is cooled
  4. extractionextracted with ethyl acetate
  5. washThe combined organic phases are washed with water and sat. aqueous sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. customthe solvent is evaporated

Sources & evidence

ORD record
ord-c7f773c4d98d4507bdd750274db8180c
Source dataset
uspto-grants-2011_08
Patent number
US08003787B2

Reaction notes

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