Water → 4-Amino-2-(methylsulfanyl)-1,3-thiazole-5-carboxamide

HRID 1958019Notes

Reaction equation

HRID 1958019 reaction equation
[C:1](/[N:3]=[C:4](/[S-:7])\[S:5][CH3:6])#[N:2].[K+].Cl[CH2:10][C:11]([NH2:13])=[O:12].C[O-].[Na+].O>C(O)C>[NH2:2][C:1]1[N:3]=[C:4]([S:5][CH3:6])[S:7][C:10]=1[C:11]([NH2:13])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6580ChloroacetamideHCID 10942334Sodium MethoxideHCID 178504096HCID 178504096, compound

Product 1

HCID 3256534-Amino-2-(methylsulfanyl)-1,3-thiazole-5-carboxamideYield 30.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of potassium (Z)-methyl cyanocarbonimidodithioate (10.0 g, 58.7 mmol) and 2-chloroacetamide (6.04 g, 64.6 mmol) in ethanol (20 mL) was refluxed for 1 h. After cooling to ambient temperature, sodium methoxide (3.49 g, 64.6 mmol) was added to the mixture. The mixture was stirred at reflux for 3 hours. The mixture was cooled to ambient temperature and water (50 mL) was added. The precipitate formed was collected by filtration. The precipitate was further washed with water and dried in vacuo. The product was obtained as a yellow solid (3.372 g, 30%). 1H NMR (300 MHz, d6-DMSO) δ 6.96 (s, 2H), 6.89 (s, 2H), 2.64 (s, 3H); LC-MS: 190 (MH+).

Workup

  1. temperaturewas refluxed for 1 h
  2. temperatureat reflux for 3 hours
  3. temperatureThe mixture was cooled to ambient temperature
  4. customThe precipitate formed
  5. filtrationwas collected by filtration
  6. washThe precipitate was further washed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-a860f07f97d4440db692b8a22268c8e8
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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