Hydrogen Sulfide → N-[(alpha-thiocarbamoyl)furfuryl]-3-methylisothiazole-5-carboxylic acid amide

HRID 1030120Notes

Reaction equation

HRID 1030120 reaction equation
[C:1]([CH:3]([NH:9][C:10]([C:12]1[S:16][N:15]=[C:14]([CH3:17])[CH:13]=1)=[O:11])[C:4]1[O:8][CH:7]=[CH:6][CH:5]=1)#[N:2].C(N(CC)CC)C.[SH2:25]>O1CCCC1>[C:1]([CH:3]([NH:9][C:10]([C:12]1[S:16][N:15]=[C:14]([CH3:17])[CH:13]=1)=[O:11])[C:4]1[O:8][CH:7]=[CH:6][CH:5]=1)(=[S:25])[NH2:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 14624283N-(alpha-cyanofurfuryl)-3-methylisothiazole-5-carboxylic acid amide

Product 1

HCID 15080081N-[(alpha-thiocarbamoyl)furfuryl]-3-methylisothiazole-5-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 g of N-(alpha-cyanofurfuryl)-3-methylisothiazole-5-carboxylic acid amide was dissolved in 30 ml of tetrahydrofuran, and 0.6 ml of triethylamine was added. With stirring at room temperature, hydrogen sulfide gas was introduced into the mixture. Five hours later, the reaction solvent was evaporated under reduced pressure. Water was added to the residue. The precipitated crystals were separated by filtration to give 1.1 g of the desired N-[(alpha-thiocarbamoyl)furfuryl]-3-methylisothiazole-5-carboxylic acid amide.

Workup

  1. customFive hours later, the reaction solvent was evaporated under reduced pressure
  2. additionWater was added to the residue
  3. customThe precipitated crystals were separated by filtration

Sources & evidence

ORD record
ord-85f5b2ecc66742409eb69360c90956d7
Source dataset
uspto-grants-1992_04
Patent number
US05104886

Reaction notes

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