2-Aminothiazole → HCID 178522563, compound

HRID 1730486Notes

Reaction equation

HRID 1730486 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[OH:7][C:8]1[C:17]2[C:12](=[C:13]([Cl:18])[CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[C:19](Cl)=[O:20]>N1C=CC=CC=1>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[NH:1][C:19]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:8]=1[OH:7])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[O:20]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 178521125HCID 178521125, compound

Product 1

HCID 178522563HCID 178522563, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 2.9 g of 2-amino-thiazole in 20 ml of pyridine was added at room temperature to a suspension of 7 g of the acid chloride of Step A in 90 ml of pyridine and the mixture was stirred for 16 hours at room temperature. The pyridine was evaporated and a mixture of potassium carbonate solution and water was added to the residue. The reaction mixture was stirred and vacuum filtered and the recovered precipitate was washed and dried. The product was crystallized from dimethylformamide to obtain 6.5 g of N-[2-thiazolyl] -4-hydroxy-8-chloro-3-quinoline-carboxamide melting above 369° C.

Workup

  1. customThe pyridine was evaporated
  2. additiona mixture of potassium carbonate solution and water
  3. additionwas added to the residue
  4. stirringThe reaction mixture was stirred
  5. filtrationvacuum filtered
  6. washthe recovered precipitate was washed
  7. customdried
  8. customThe product was crystallized from dimethylformamide

Sources & evidence

ORD record
ord-51cf3fe9eb494e639301eb2a80dbcd34
Source dataset
uspto-grants-1976_11
Patent number
US03992540

Reaction notes

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