Dimethylformamide → HCID 12843951, compound

HRID 1633174Notes

Reaction equation

HRID 1633174 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:4]=1[NH2:5].CN(C=O)C.[CH2:18]([O:25][C:26](Cl)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH3:1][O:2][C:3]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:4]=1[NH:5][C:26](=[O:27])[O:25][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 73372-Methoxy-4-nitroanilineHCID 10387Benzyl chloroformate

Product 1

HCID 12843951HCID 12843951, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Methoxy-4-nitroaniline, 51 g (0.3 mol), was dissolved in 135 ml of acetone containing 12 g of MgO, and 65 ml of commercial benzylchloroformate was slowly added to the stirred mixture. After 4 hours the flask was warmed to redissolve the precipitate and the mixture was stirred overnight. DMF (100 ml) was added, and the mixture was heated to dissolve all of the product before being filtered through celite. After dilution with 250 ml of ethanol the hot solution was further diluted with water until almost cloudy, and allowed to cool. The pale yellow crystals were collected, washed well with 50% aqueous ethanol, and dried. Yield 86.0 g, 94%, m.p. 130°-131° C.

Workup

  1. additionwas slowly added to the stirred mixture
  2. temperatureAfter 4 hours the flask was warmed
  3. dissolutionto redissolve the precipitate
  4. temperaturethe mixture was heated
  5. dissolutionto dissolve all of the product
  6. filtrationbefore being filtered through celite
  7. additionAfter dilution with 250 ml of ethanol the hot solution was further diluted with water until almost cloudy
  8. temperatureto cool
  9. customThe pale yellow crystals were collected
  10. washwashed well with 50% aqueous ethanol
  11. customdried

Sources & evidence

ORD record
ord-9ed3dbf6b9e246b7a583367a44af3faf
Source dataset
uspto-grants-1984_10
Patent number
US04479000

Reaction notes

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