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

HRID 462147Notes

Reaction equation

HRID 462147 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-273833c9c1fc4afeb25732ae8da2b3d8
Source dataset
uspto-grants-1977_12
Patent number
US04065500

Reaction notes

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