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

HRID 1111407Notes

Reaction equation

HRID 1111407 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-e4c7a4f7ea3d4b30841898f512ca6111
Source dataset
uspto-grants-1990_12
Patent number
US04980363

Reaction notes

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