Dimethylformamide → HCID 10421086, compound

HRID 1283781Notes

Reaction equation

HRID 1283781 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:13][N:14]([CH3:17])[CH:15]=O>>[CH3:13][N:14]([CH3:17])/[CH:15]=[CH:1]/[C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 793303-Methyl-4-nitroanisole

Product 1

HCID 10421086HCID 10421086, compoundYield 36%

Procedure

A solution of 3.0 g. of 3-methyl-4-nitroanisole, 5.1 g. of N,N-dimethylformaide dicyclohexyl acetal, and 25 ml. of N,N-dimethylformamide was heated at reflux under a nitrogen atmosphere for 40 hours and then was transferred to a Claisen flask. Vacuum distillation gave, after removal of the volatile components, 1.89 g. of a red liquid (b.p. 158°/0.04 mm.) which crystallized on scratching to give a solid, having a melting point of 61°-64°. Recrystallization from 10 ml. of ether and 7 ml. of petroleum ether gave 1.46 g (36%) of trans-β-dimethylamino-5-methoxy-2-nitrostyrene having a melting point of 67.5°-69°.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for 40 hours
  2. distillationVacuum distillation
  3. customgave
  4. customafter removal of the volatile components, 1.89 g
  5. customof a red liquid (b.p. 158°/0.04 mm.) which crystallized
  6. customto give a solid
  7. customRecrystallization from 10 ml

Sources & evidence

ORD record
ord-b6844719bb074321a062f0b254c9edca
Source dataset
uspto-grants-1976_08
Patent number
US03976639

Reaction notes

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