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Water → HCID 86736628, compound

HRID 1862788
Notes
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Reaction equation

HRID 1862788 reaction equation
O[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.[OH2:33]>C(Cl)Cl>[CH3:22][S:23]([O:25][C: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])[C:3]([NH:2][CH3:21])=[O:20])(=[O:33])=[O:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

HCID 86736628HCID 86736628, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

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,1) isomer form.

Workup

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

Sources & evidence

ORD record
ord-d8a58a54b4ac45fdb74ebbfa75307b36
Source dataset
uspto-grants-1979_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04166734

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes