Dimethylformamide dimethyl acetal → N'-(4-BroMo-2-cyanophenyl)-N,N-diMethylforMiMidaMide

HRID 1675720Notes

Reaction equation

HRID 1675720 reaction equation
[C:1]([C:3]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:4]=1[NH2:5])#[N:2].CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>CCCCCC>[Br:10][C:8]1[CH:7]=[CH:6][C:4]([N:5]=[CH:13][N:14]([CH3:16])[CH3:15])=[C:3]([C:1]#[N:2])[CH:9]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 4297402-Amino-5-bromobenzonitrile

Product 1

HCID 57857968N'-(4-BroMo-2-cyanophenyl)-N,N-diMethylforMiMidaMideYield 85.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

59 g (300 mmol) of 2-cyano-4-bromoaniline are suspended in 35 ml of dimethylformamide dimethyl acetal (780 mmol) and heated under reflux for 1.5 h. The resulting mixture is cooled and then 300 ml of hexane are added. The resulting solid is filtered off and washed with hexane. 64.5 g (85%) of the desired product are obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 h
  3. temperatureThe resulting mixture is cooled
  4. filtrationThe resulting solid is filtered off
  5. washwashed with hexane

Sources & evidence

ORD record
ord-792904f5843f4ab5a7bd557ffcb17e67
Source dataset
uspto-grants-2011_08
Patent number
US08003787B2

Reaction notes

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