Methyl nitrite → HCID 73081857, compound

HRID 1087233Notes

Reaction equation

HRID 1087233 reaction equation
[N:1](OC)=[O:2].[F:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[S:13][C:14]1[CH:24]=[C:23]([C:25](=[O:28])[CH2:26][CH3:27])[CH:22]=[CH:21][C:15]=1[NH:16][S:17]([CH3:20])(=[O:19])=[O:18]>O1CCCC1.Cl.CCOCC>[F:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[S:13][C:14]1[CH:24]=[C:23]([C:25](=[O:28])[C:26](=[N:1][OH:2])[CH3:27])[CH:22]=[CH:21][C:15]=1[NH:16][S:17]([CH3:20])(=[O:19])=[O:18]

Participants

6

Reactant 2

HCID 12231Methyl nitriteHCID 11726686HCID 11726686, compound

Product 1

HCID 73081857HCID 73081857, compoundYield 91.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
3 °C

Procedure

Methyl nitrite [prepared from sodium nitrite (1.4 g), methanol (0.9 ml) and sulfuric acid (0.7 ml) in water (2.3 ml)] was introduced into an ice-cooled mixture of 2'-(2,4-difluorophenylthio)-4'-propionylmethanesulfonanilide (2.54 g) in tetrahydrofuran (10 ml) and 12% hydrogen chloride in ether (10 ml). The mixture was stirred for 5 hours at 3° C. and evaporated. The residual solid was recrystallized from ethanol to give colorless crystals of 2'-(2,4-difluorophenylthio)-4'[2-(hydroxyimino)-1-oxopropyl]methanesulfonanilide (2.5 g).

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe residual solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-78170ce767174f60989fe7573789dd3b
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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