Ethyl chloroformate → N1-ethoxycarbonyl-N1-methyl-3,5-dinitro-N4,N4-di-n-propylsulfanilamide

HRID 918352Notes

Reaction equation

HRID 918352 reaction equation
C[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[C:10]([N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[C:9]([N+:22]([O-:24])=[O:23])=[CH:8][C:3]=1[S:4]([NH2:7])(=[O:6])=[O:5].Cl[C:26]([O:28][CH2:29][CH3:30])=[O:27].[C:31](=O)([O-])[O-].[K+].[K+]>C(COC)OC>[CH2:29]([O:28][C:26]([N:7]([CH3:31])[S:4](=[O:5])([C:3]1[CH:8]=[C:9]([N+:22]([O-:24])=[O:23])[C:10]([N:15]([CH2:16][CH2:17][CH3:18])[CH2:19][CH2:20][CH3:21])=[C:11]([N+:12]([O-:14])=[O:13])[CH:2]=1)=[O:6])=[O:27])[CH3:30]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 21433414methyl-3,5-dinitro-N4,N4-dipropylsulfanilamide

Product 1

HCID 54456851N1-ethoxycarbonyl-N1-methyl-3,5-dinitro-N4,N4-di-n-propylsulfanilamide

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3.6 g (0.01 mol) N1 methyl-3,5-dinitro-N4,N4 -dipropylsulfanilamide, 2.2 g (0.02 mol) ethyl chloroformate, 2.8 g (0.02 mol) potassium carbonate, and 50 ml dimethoxyethane was heated at reflux until gas evolution ceased. The reaction mixture was filtered and evaporated under reduced pressure. The residue was recrystallized from ethanol to give 2.5 g of the product, m.p. 104°C (dec.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux until gas evolution
  3. filtrationThe reaction mixture was filtered
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-df42facd38824851aa702f1512c698e8
Source dataset
uspto-grants-1976_07
Patent number
US03971650

Reaction notes

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