Hydrogen Sulfide → 2-Cyclopropylamino-4-methyl-thiazole-5-carboxylic acid (thiocarbamoyl-thiophen-2-yl-methyl)-amide

HRID 439301Notes

Reaction equation

HRID 439301 reaction equation
[C:1]([CH:3]([NH:9][C:10]([C:12]1[S:16][C:15]([NH:17][CH:18]2[CH2:20][CH2:19]2)=[N:14][C:13]=1[CH3:21])=[O:11])[C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)#[N:2].C(N(CC)CC)C.[SH2:29]>C(O)C>[C:1]([CH:3]([NH:9][C:10]([C:12]1[S:16][C:15]([NH:17][CH:18]2[CH2:20][CH2:19]2)=[N:14][C:13]=1[CH3:21])=[O:11])[C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)(=[S:29])[NH2:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 543672022-Cyclopropylamino-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl)-amide

Product 1

HCID 543298972-Cyclopropylamino-4-methyl-thiazole-5-carboxylic acid (thiocarbamoyl-thiophen-2-yl-methyl)-amideYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.72g of 2-cyclopropylamino-4-methyl-thiazole-5-carboxylic acid (cyano-thiophen-2-yl-methyl)-amide (12) was dissolved in 10ml of ethanol and then 0.63ml of triethylamine was added thereto. The reaction solution was stirred under reflux for 8 hours while introducing hydrogen sulfide gas. After removing the solvent, water was added to the residue and then the solid product which is not dissolved in water was filtered. The filtered solid product was washed with diethylether and then dried to obtain 0.70g (Yield 88%) of the title compound.

Workup

  1. temperatureunder reflux for 8 hours
  2. customAfter removing the solvent, water
  3. additionwas added to the residue
  4. dissolutionthe solid product which is not dissolved in water
  5. filtrationwas filtered
  6. washThe filtered solid product was washed with diethylether
  7. customdried

Sources & evidence

ORD record
ord-e50cfb74c4cd4ca6b45e05c723e1a1f7
Source dataset
uspto-grants-1996_05
Patent number
US05514643

Reaction notes

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