Pyridine → HCID 15729164, compound

HRID 1656964Notes

Reaction equation

HRID 1656964 reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:5][N:6]=1.N1C=CC=CC=1.[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>CN(C)C=O>[F:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:1][C:2]2[S:3][C:4]([S:7][C:8]3[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=3)=[CH:5][N:6]=2)=[O:26])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 678794-Fluorobenzoyl chlorideHCID 15729152HCID 15729152, compound

Product 1

HCID 15729164HCID 15729164, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-amino-5-(4-pyridylthio)thiazole (2.5 g) and pyridine (3 g) in N,N-dimethylformamide (25 ml) was added dropwise the 4-fluorobenzoyl chloride (2.7 g) at 5° C. under ice cooling with stirring. The mixture was stirred at 5° C. for 4 hours under ice cooling. The reaction mixture was concentrated under reduced pressure and the residue was triturated with water. The precipitates were collected by filtration, washed with water and dried in vacuo to give 2-(4-fluorobenzoylamino)-5-(4-pyridylthio)thiazole (2.5 g, yield: 63.1%). mp: 220°-225° C. (dec.)

Workup

  1. stirringThe mixture was stirred at 5° C. for 4 hours under ice cooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was triturated with water
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-1238113be66c414eb91edb0919918cd9
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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