Water → 2-Acetamido-5-(2-pyrimidinylthio)thiazole

HRID 1656960Notes

Reaction equation

HRID 1656960 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7](Cl)=[CH:8][N:9]=1)(=[O:3])[CH3:2].[SH:11][C:12]1[N:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][C:7]([S:11][C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 46841342-Acetamido-5-chlorothiazoleHCID 178418793HCID 178418793, compound

Product 1

HCID 157291582-Acetamido-5-(2-pyrimidinylthio)thiazoleYield 60.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-acetamido-5-chlorothiazole (14.3 g), 2-mercaptopyrimidine (10 g) and potassium carbonate anhydrous (22.4 g) in N,N-dimethylformamide (280 ml) was stirred at 150° C. an hour. The reaction mixture was poured into water with stirring under ice cooling. The mixture was extracted with ethyl acetate, washed with water and dried over magnesium sulfate. The organic layer was concentrated under reduced pressure to give solid. The solid was triturated with water, and the precipitates were collected by filtration, washed with water and dried in vacuo to give 2-acetamido-5-(2-pyrimidinylthio)thiazole (12.30 g, yield: 60.2%). mp: 225° C. (dec.) IR (Nujol): 3170, 1645, 1555, 1310 cm-1

Workup

  1. stirringwith stirring under ice cooling
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customto give solid
  7. customThe solid was triturated with water
  8. filtrationthe precipitates were collected by filtration
  9. washwashed with water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-494d115f616a481fafcbfe13e6613866
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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