Pyridine → HCID 15729154, compound

HRID 2380601Notes

Reaction equation

HRID 2380601 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:5][N:6]=1.N1C=CC=CC=1.[C:23](Cl)(=[O:26])[CH2:24][CH3:25].C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:23]([NH:1][C:2]1[S:3][C:4]([S:7][C:8]2[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=2)=[CH:5][N:6]=1)(=[O:26])[CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 350381HCID 350381, compoundHCID 516892Sodium Bicarbonate

Product 1

HCID 15729154HCID 15729154, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-amino-5-(4-nitrophenylthio)thiazole (2.6 g) and pyridine (1 g) in N,N-dimethylformamide (30 ml) was added dropwise the propionylchloride (1.1 g) at 5° C. under ice cooling with stirring. The mixture was stirred at 5° C. for 3.5 hours. The reaction mixture was poured into ice water and the mixture was adjusted to pH 8 using aqueous sodium bicarbonate. The precipitates were collected by filtration, washed with water and dried in vacuo to give 2-propionylamino-5-(4-nitrophenylthio)thiazole (2.5 g, yield: 78.7%).

Workup

  1. stirringThe mixture was stirred at 5° C. for 3.5 hours
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-91f9b844ccc240139cc37b356ab5b895
Source dataset
uspto-grants-1994_11
Patent number
US05369107

Reaction notes

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