Sodium Acetate → HCID 15729142, compound

HRID 1656936Notes

Reaction equation

HRID 1656936 reaction equation
Cl[CH2:2][C:3](=O)[C:4]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[O:5].[NH2:16][C:17]([NH2:19])=[S:18].C([O-])(=O)C.[Na+]>C(O)C>[NH2:19][C:17]1[S:18][CH:2]=[C:3]([C:4](=[O:5])[C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)[N:16]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2723790ThioureaHCID 18954740HCID 18954740, compound

Product 1

HCID 15729142HCID 15729142, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of chloromethyl-(4-nitrophenyl)diketone (2 g), thiourea (1.5 g) and sodium acetate (1.6 g) in ethanol (20 ml) was heated at 50° C. for 4 hours with stirring. The mixture was concentrated in vacuo and the residue was triturated with water. The precipitates were collected by filtration, washed with water and dried in vacuo to give solid. The solid was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 100 g) and eluted with a mixture of chloroform and methanol (10:1). The fractions containing the objective compound were combined and concentrated under reduced pressure to give 2-amino-4-(4-nitrobenzoyl)thiazole (0.71 g, yield: 32.4%). mp: 194°-198° C. (dec.) IR (Nujol): 3300-3450, 1660, 1600, 1520, 1350 cm-1

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was triturated with water
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customto give solid
  7. washeluted with a mixture of chloroform and methanol (10:1)
  8. additionThe fractions containing the objective compound
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c3049e63c1145108597ed478178959c
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

Loading…