Propyl chloroformate → N-propoxycarbonyl-N1-methyl-3,5-dinitro-N4,N4-di-n-propylsulfanilamide

HRID 918353Notes

Reaction equation

HRID 918353 reaction equation
[CH3:1][NH:2][S:3](=[O:24])([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[C:7]([N+:21]([O-:23])=[O:22])[CH:6]=1)=[O:4].Cl[C:26]([O:28][CH2:29][CH2:30][CH3:31])=[O:27].C(=O)([O-])[O-].[K+].[K+]>C(COC)OC>[CH2:29]([O:28][C:26]([N:2]([CH3:1])[S:3](=[O:24])([C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])=[C:7]([N+:21]([O-:23])=[O:22])[CH:6]=1)=[O:4])=[O:27])[CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 7998Propyl chloroformateHCID 11430Potassium CarbonateHCID 10428592Benzenesulfonamide, 4-(dipropylamino)-N-methyl-3,5-dinitro-

Product 1

HCID 53885645N-propoxycarbonyl-N1-methyl-3,5-dinitro-N4,N4-di-n-propylsulfanilamideYield 80.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4.5 g (0.0125 mol) N1 -methyl-3,5-dinitro-N4,N4 -dipropylsulfanilamide, 3.06 g (0.025 mol) n-propyl chloroformate, 3.5 g (0.025 mol) potassium carbonate, and 75 ml dimethoxyethane was heated at reflux for 2 hours. The reaction mixture was filtered and evaporated under reduced pressure. The residue was recrystallized from ethanol to give 4.5 g of the product, m.p. 110°-113°C, as an orange solid.

Workup

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

Sources & evidence

ORD record
ord-a0ca3bb16cdf454e9a29fbc907ee12d7
Source dataset
uspto-grants-1976_07
Patent number
US03971650

Reaction notes

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