Dimethylformamide dimethyl acetal → N'-(2-cyano-4-methoxy-5-benzyloxyphenyl)-N,N-dimethylimidoformamide

HRID 749153Notes

Reaction equation

HRID 749153 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([O:18][CH3:19])=[CH:6][C:3]=1[C:4]#[N:5].CO[CH:22](OC)[N:23]([CH3:25])[CH3:24]>C1(C)C=CC=CC=1>[CH2:11]([O:10][C:8]1[C:7]([O:18][CH3:19])=[CH:6][C:3]([C:4]#[N:5])=[C:2]([N:1]=[CH:22][N:23]([CH3:25])[CH3:24])[CH:9]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 117015842-Amino-4-(benzyloxy)-5-methoxybenzonitrile

Product 1

HCID 11609261N'-(2-cyano-4-methoxy-5-benzyloxyphenyl)-N,N-dimethylimidoformamideYield 90.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

2-amino-4-(benzyloxy)-5-methoxybenzonitrile (100 g, 394 mmol) in toluene (1400 ml) was treated with dimethylformamide dimethylacetal (100 ml, 940 mmol) at reflux with slow distillation of solvent to maintain the internal temperature at 105° C. After 3 hours the solution was cooled and filtered to remove a small amount of solid. The filtrate was evaporated in vacuo, the residue triturated with diethyl ether, the solid collected by suction filtration and dried in vacuo to yield N′-(5-(benzyloxy)-2-cyano-4-methoxyphenyl)-N,N-dimethylimidoformamide (110 g, 90% yield) as a brown solid:

Workup

  1. temperatureat reflux with slow distillation of solvent
  2. temperatureAfter 3 hours the solution was cooled
  3. filtrationfiltered
  4. customto remove a small amount of solid
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue triturated with diethyl ether
  7. filtrationthe solid collected by suction filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-9213ff80dcde4cb19d267ac18dca3cc8
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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