Dimethylformamide → Trans-beta-dimethylamino-4-methyl-2-nitrostyrene

HRID 1447315

반응식

HRID 1447315 반응식
[N+:1]([C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[CH3:11])([O-:3])=[O:2].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16].CN(C)C=O>CO>[CH3:14][N:15]([CH3:17])/[CH:16]=[CH:11]/[C:5]1[CH:6]=[CH:7][C:8]([CH3:10])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 6974Nitro-p-xyleneHCID 78373Dimethylformamide dimethyl acetal

생성물 1

HCID 20550574Trans-beta-dimethylamino-4-methyl-2-nitrostyrene수율 83%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

A 12-l. three-necked flask, equipped with a thermometer, a mechanical stirrer and a 60 cm. vacuum-jacketed silvered column with glass helice packing connected to a total-condensation, variable take-off still head with receiver was charged under nitrogen with 675 g (4.46 moles) of 2-nitro-1,4-dimethylbenzene, 736 g (6.17 moles) of N,N-dimethylformamide dimethyl acetal and 3.0 l of N,N-dimethylformamide. The mixture was stirred and heated with a heating mantle for 37 hours. The pot temperature was gradually raised from 130° and 144° while the formed methanol was removed by distillation. The fractionating column was replaced by a distilling head with condenser and receiver (cooled in a dry ice-acetone bath). The dimethylformamide was removed by distillation, first at aspirator vacuum and then at high vacuum (water bath 70°), giving a residue of 924 g (100%) of crude product as a dark red viscous oil. This material was poured into a beaker and mixed thoroughly with 640 ml of methyl alcohol. The mixture was stirred in an ice bath until the product crystallized in mass and was then refrigerated overnight. The precipitate was collected by suction filtration, washed with 320 ml of methyl alcohol and dried in vacuo at room temperature (constant weight) to afford 760 g (83%) of product as a free-flowing, dark-red crystalline solid, m.p. 41.5°-43.5° C.

후처리

  1. customthree-necked flask, equipped with a thermometer, a mechanical stirrer
  2. customvacuum-jacketed silvered column with glass helice packing connected to a total-condensation, variable take-off still head with receiver
  3. temperatureheated with a heating mantle for 37 hours
  4. customwas removed by distillation
  5. customThe fractionating column was replaced by a distilling head with condenser
  6. temperaturereceiver (cooled in a dry ice-acetone bath)
  7. customThe dimethylformamide was removed by distillation, first at aspirator vacuum
  8. customat high vacuum (water bath 70°), giving a residue of 924 g (100%) of crude product as a dark red viscous oil
  9. additionThis material was poured into a beaker
  10. stirringThe mixture was stirred in an ice bath until the product
  11. customcrystallized in mass
  12. customrefrigerated overnight
  13. filtrationThe precipitate was collected by suction filtration
  14. washwashed with 320 ml of methyl alcohol
  15. customdried in vacuo at room temperature (constant weight)

출처 및 근거

ORD 기록
ord-5668d8a59cda44e180be6d212fcf0389
출처 데이터셋
uspto-grants-1982_02
특허 번호
US04316847

연결된 노트

불러오는 중…