2-Furancarbonyl chloride → HCID 698244, compound

HRID 1112106Notes

Reaction equation

HRID 1112106 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[CH3:9][NH:10][C:11](=[S:14])[NH:12][NH2:13]>N1C=CC=CC=1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:13][NH:12][C:11]([NH:10][CH3:9])=[S:14])=[O:7]

Participants

4

Reactant 2

HCID 682422-Furancarbonyl chlorideHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 698244HCID 698244, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Furoyl chloride (31 g. or 0.238 mole) was added dropwise to a slurry of 4-methylthiosemicarbazide (25 g. or 0.238 moles) in dry pyridine (200 ml.) cooled to -10°. The slurry was allowed to come to ambient temperature and stirred overnight. The reaction mixture was poured into 1500 ml. of crushed ice, the precipitate was collected, dried and recrystallized from EtOH to give 1-(2-furoyl)-4-methyl thiosemicarbazide (28.0 g.). This melted at 204°-206° C. (dec.) and was found to contain by analysis 42.4% C, 4.6% H, 21.2% N, 16.1% O, 15.9% S; C7H9N3O2S requires 42.2% C, 4.5% H, 21.1% N, 16.1% O, 16.1% S. The structure was confirmed by its infrared spectrum and nuclear magnetic resonance spectrum.

Workup

  1. temperaturecooled to -10°
  2. customto come to ambient temperature
  3. additionThe reaction mixture was poured into 1500 ml
  4. customof crushed ice, the precipitate was collected
  5. customdried
  6. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-2c8d46e20dcd424195c6d812152174d8
Source dataset
uspto-grants-1978_10
Patent number
US04120864

Reaction notes

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