Water → HCID 23345844, compound

HRID 1856094Notes

Reaction equation

HRID 1856094 reaction equation
[OH:1][N:2]([CH3:21])[C:3](=[O:20])[CH:4]([NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]([CH3:16])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18])[CH3:5].[CH3:22][S:23](Cl)(=[O:25])=[O:24].CN1C=CN=C1.O>C(Cl)Cl>[CH3:22][S:23]([O:1][N:2]([CH3:21])[C:3](=[O:20])[CH:4]([NH:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]([CH3:16])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18])[CH3:5])(=[O:25])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 13901-MethylimidazoleHCID 31297Methanesulfonyl chlorideHCID 20532869HCID 20532869, compound

Product 1

HCID 23345844HCID 23345844, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.8 g of N-hydroxy-N-methyl-2-(4-methyl-2,6-dinitrophenylamino)propanamide in 50 ml methylene chloride was added at room temperature to a stirred suspension of the product prepared from 1.4 g methane sulfonyl chloride and 0.8 g N-methylimidazole. After 3 hours the resulting mixture was poured into water. The methylene chloride layer was evaporated to dryness and the residue was crystallized from ethanol to give a 0.8 g (22% yield) of product as a yellow solid; m.p. 145° C. with decomposition, (d,l) isomer form.

Workup

  1. customThe methylene chloride layer was evaporated to dryness
  2. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-1edaf31d783b4086b1e01e5d746e8353
Source dataset
uspto-grants-1980_08
Patent number
US04218239

Reaction notes

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