Methanol → HCID 20371102, compound

HRID 616120Notes

Reaction equation

HRID 616120 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH:13]=[CH2:14])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])(=O)C.CO.[OH-].[Na+]>O>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH:13]=[CH2:14])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 14273283N-{2-Nitro-4-[(prop-2-en-1-yl)sulfanyl]phenyl}acetamide

Product 1

HCID 20371102HCID 20371102, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 G. of 1-acetamido-2-nitro-4-(prop-2-en-1-ylthio)-benzene is treated with 20 ml. methanol and 10 ml. 5N aqueous sodium hydroxide at 20°-25° C for one hour. The mixture is diluted with water and the crude product filtered off. Recrystallization from benzene yields 1-amino-2-nitro-4-(prop-2-en-1-ylthio)benzene. This latter compound in 200 ml. acetone is treated with 4 g. methoxy carbonyl isothiocyanate at room temperatue for several days (i.e., until no starting material is present). The mixture is concentrated and the residue triturated with methanol to yield 1-(3-methoxycarbonyl-2-thioureido)-2-nitro-4-(prop-2-en-1-ylthio)benzene.

Workup

  1. filtrationthe crude product filtered off
  2. customRecrystallization from benzene

Sources & evidence

ORD record
ord-c6e7658458f34583b057d792ff7b6de9
Source dataset
uspto-grants-1978_02
Patent number
US04072696

Reaction notes

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