N-(2-amino-2-thioxoethyl)acetamide → HCID 18956300, compound

HRID 2379827Notes

Reaction equation

HRID 2379827 reaction equation
Br.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=O)[CH2:9]Br)[N:7]=1.[C:12]([CH2:15][NH:16][C:17](=[O:19])[CH3:18])(=[S:14])[NH2:13]>C(O)C>[C:17]([NH:16][CH2:15][C:12]1[S:14][CH:9]=[C:8]([C:6]2[N:7]=[C:3]([NH2:2])[S:4][CH:5]=2)[N:13]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 4435531N-(2-amino-2-thioxoethyl)acetamideHCID 18956304HCID 18956304, compound

Product 1

HCID 18956300HCID 18956300, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-amino-4-bromoacetylthiazole hydrobromide (14.0 g) and N-[(thiocarbamoyl)methyl]-acetamide (6.1 g) in ethanol (300 ml) was stirred at room temperature for 24 hours. The insoluble material was removed by filtration. The solvent was removed under reduced pressure. The residue was suspended in water (300 ml). The mixture was alkalized to pH 10 with a saturated aqueous potassium carbonate solution and then was extracted with a mixture of ethyl acetate (500 ml) and tetrahydrofuran (100 ml). The extract was dried over magnesium sulfate and then was evaporated to afford 4-(2-acetylaminomethylthiazol-4-yl)-2-aminothiazole (5.83 g).

Workup

  1. customThe insoluble material was removed by filtration
  2. customThe solvent was removed under reduced pressure
  3. extractionwas extracted with a mixture of ethyl acetate (500 ml) and tetrahydrofuran (100 ml)
  4. dry with materialThe extract was dried over magnesium sulfate
  5. customwas evaporated

Sources & evidence

ORD record
ord-0577b30e88e84864981085cef14fde49
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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