2-Furancarbonyl chloride → HCID 698244, compound

HRID 1680091Notes

Reaction equation

HRID 1680091 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. (doc.) and was found to contain by analysis 42.4% C, 4.6% H, 21.2%, N, 16.1%, O, 15.9% S; C7H9X3O2S 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-bcb2a1cf8bf74441ae0fb94fd05432c3
Source dataset
uspto-grants-1981_06
Patent number
US04271308

Reaction notes

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