Acetone → HCID 178482501, compound

HRID 67730Notes

Reaction equation

HRID 67730 reaction equation
[CH3:1][NH:2][C:3](=[S:6])[NH:4][NH2:5].[CH3:7][C:8]([CH3:10])=O.N1C=CC=CC=1.[N+:17]([C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24])([O-:19])=[O:18]>O>[CH3:7][C:8]1([CH3:10])[S:6][C:3]([NH:2][CH3:1])=[N:4][N:5]1[C:23](=[O:24])[C:22]1[CH:26]=[CH:27][CH:28]=[C:20]([N+:17]([O-:19])=[O:18])[CH:21]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 1049PyridineHCID 8495Benzoyl chloride, 3-nitro-HCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 178482501HCID 178482501, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 21 g. portion of 4-methylthiosemicarbazide was reacted with 200 ml. of acetone at ambient temperature for 16 hours, and then 16 ml. of pyridine and 37.1 g. of 3-nitrobenzoyl chloride were added and the mixture was stirred for 3 hours at ambient temperature. Two hundred ml. of water was added, the mixture was stirred for 1 hour, the layers were separated, and the organic layer was evaporated to an oil under vacuum. The oil solidified upon standing overnight, and was recrystallized from hot acetone to obtain 26.3 g. of crude product, which was recrystallized again from 15 ml. of hot nitromethane to obtain 21.4 g. of product, m.p. 130°-133°.

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. customthe layers were separated
  3. customthe organic layer was evaporated to an oil under vacuum
  4. waitupon standing overnight
  5. customwas recrystallized from hot acetone
  6. customto obtain 26.3 g
  7. customof crude product, which was recrystallized again from 15 ml
  8. customof hot nitromethane to obtain 21.4 g

Sources & evidence

ORD record
ord-217dee8cec9349d889f6c8eae89a5d30
Source dataset
uspto-grants-1982_08
Patent number
US04346225

Reaction notes

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