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

HRID 1973209

반응식

HRID 1973209 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-nitrobenzyl chloride, 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-905072201a864ee1a2e09573ddf44e75
출처 데이터셋
uspto-grants-1976_12
특허 번호
US03996282

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