N-{[5-(2-chloroacetyl)furan-2-yl]methyl}acetamide → 4-(5-Acetylaminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole

HRID 1033048

Reaction equation

HRID 1033048 reaction equation
[C:1]([NH:4][CH2:5][C:6]1[O:10][C:9]([C:11](=O)[CH2:12]Cl)=[CH:8][CH:7]=1)(=[O:3])[CH3:2].[NH2:15][C:16](=[N:18][C:19]([NH2:21])=[S:20])[NH2:17]>C(O)C>[C:1]([NH:4][CH2:5][C:6]1[O:10][C:9]([C:11]2[N:21]=[C:19]([N:18]=[C:16]([NH2:17])[NH2:15])[S:20][CH:12]=2)=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2393628N-{[5-(2-chloroacetyl)furan-2-yl]methyl}acetamideHCID 2724563Amidinothiourea

Product 1

HCID 117783664-(5-Acetylaminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazoleYield 46.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-acetylaminomethyl-2-chloroacetylfuran (39.9 g) and diaminomethylenethiourea (21.9 g) in ethanol (400 ml) was refluxed for two hours with stirring. The solvent was evaporated in vacuo and the residue was dissolved in water (300 ml). The solution was basified with an aqueous potassium carbonate. The resulting precipitate was collected by filtration, washed with water and recrystallized from a mixture of methanol, tetrahydrofuran and diisopropyl ether to afford 4-(5-acetylaminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (24.1 g).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in water (300 ml)
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customrecrystallized from a mixture of methanol, tetrahydrofuran and diisopropyl ether

Sources & evidence

ORD record
ord-8a22acb0dcf145649c406210ab4bf3a1
Source dataset
uspto-grants-1994_05
Patent number
US05308857

Linked notes

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