4-(Chloromethyl)-2-nitroanisole → Benzenemethanaminium, N,N-bis[3-(formylamino)propyl]-4-methoxy-N-methyl-3-nitro-, chloride (1:1)

HRID 1580923

반응식

HRID 1580923 반응식
[CH:1]([NH:3][CH2:4][CH2:5][CH2:6][N:7]([CH3:14])[CH2:8][CH2:9][CH2:10][NH:11][CH:12]=[O:13])=[O:2].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][Cl:22])=[CH:19][C:18]=1[N+:25]([O-:27])=[O:26]>C(#N)C>[Cl-:22].[CH3:14][N+:7]([CH2:21][C:20]1[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[C:18]([N+:25]([O-:27])=[O:26])[CH:19]=1)([CH2:6][CH2:5][CH2:4][NH:3][CH:1]=[O:2])[CH2:8][CH2:9][CH2:10][NH:11][CH:12]=[O:13]

참가 물질

4

반응물 2

HCID 807854-(Chloromethyl)-2-nitroanisoleHCID 3084810Formamide, N,N'-[(methylimino)di-3,1-propanediyl]bis-

생성물 1

HCID 100848Benzenemethanaminium, N,N-bis[3-(formylamino)propyl]-4-methoxy-N-methyl-3-nitro-, chloride (1:1)

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

A mixture of 54.0 parts of N,N-bis(3-formamidopropyl)methylamine, 50.4 parts of 4-methoxy-3-nitrobenzylchloride, and 78 parts of acetonitrile was stirred at reflux for seven and a half hours. An additional 78 parts of acetonitrile was added to the reaction mixture causing an oil to separate. Heating at reflux was continued for an additional two hours and the 140 parts of acetonitrile was distilled away and 200 parts of water was added. The remaining acetonitrile was removed by distillation and the cooled reaction mixture was filtered with the aid of diatomaceous earth to obtain an aqueous solution of N-methyl-N-(3-nitro-4-methoxybenzyl)-N,N-bis(3-formamidopropyl)ammonium chloride. The solution was used directly for reduction of the nitro group.

후처리

  1. temperatureat reflux for seven and a half hours
  2. customto separate
  3. temperatureHeating
  4. temperatureat reflux
  5. distillationthe 140 parts of acetonitrile was distilled away
  6. addition200 parts of water was added
  7. customThe remaining acetonitrile was removed by distillation
  8. customthe cooled reaction mixture
  9. filtrationwas filtered with the aid of diatomaceous earth

출처 및 근거

ORD 기록
ord-82b97142c6844cd6a9ed5843d4a32c21
출처 데이터셋
uspto-grants-1976_01
특허 번호
US03935182

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