6-Nitro-m-toluidine → Isopropylidene (5-methyl-2-nitroanilino)methylenemalonate

HRID 613562노트

반응식

HRID 613562 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[CH3:12][C:13]1([CH3:21])[O:18][C:17](=[O:19])[CH2:16][C:15](=[O:20])[O:14]1.[CH:22](OCC)(OCC)OCC>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH:7][CH:22]=[C:16]1[C:17](=[O:19])[O:18][C:13]([CH3:21])([CH3:12])[O:14][C:15]1=[O:20]

참가 물질

5

반응물 3

HCID 113566-Nitro-m-toluidineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformate

생성물 1

HCID 53705573Isopropylidene (5-methyl-2-nitroanilino)methylenemalonate수율 75.5%

시약·촉매·용매 1

HCID 702Ethanol용매3회

실험 절차

To a stirred suspension of 5-methyl-2-nitroaniline (10.0 g) in ethanol (20 ml) were added 2,2-dimethyl-1,3-dioxane-4,6-dione (9.95 g) and triethyl orthoformate (10.7 g) at 50° C. The resulting mixture was heated at 120° C. for one hour during which time ethanol (20 ml) was added to the mixture and ethanol liberated was distilled off. After cooling, ethyl acetate (40 ml) was added thereto and the resulting precipitate was collected by filtration. The solid was washed with hot ethanol (40 ml) and allowed to cool to ambient temperature. The precipitate was collected by filtration and air-dried to afford isopropylidene (5-methyl-2-nitroanilino)methylenemalonate (15.2 g) as yellow needles.

후처리

  1. distillationliberated was distilled off
  2. temperatureAfter cooling
  3. additionethyl acetate (40 ml) was added
  4. filtrationthe resulting precipitate was collected by filtration
  5. washThe solid was washed with hot ethanol (40 ml)
  6. filtrationThe precipitate was collected by filtration
  7. customair-dried

출처 및 근거

ORD 기록
ord-caf00fac7d5440259ad637ff373070c2
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06008230

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