HCID 178508561, compound → HCID 178522562, compound

HRID 2419799Notes

Reaction equation

HRID 2419799 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16](Cl)=[O:17].[NH:19]=[C:20]1[NH:24][CH2:23][CH2:22][S:21]1>N1C=CC=CC=1>[S:21]1[CH2:22][CH2:23][N:24]=[C:20]1[NH:19][C:16]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[OH:1])=[CH:10][CH:9]=[CH:8][C:7]=2[C:12]([F:15])([F:14])[F:13])=[O:17]

Participants

4

Reactant 2

HCID 178508561HCID 178508561, compoundHCID 178521124HCID 178521124, compound

Product 1

HCID 178522562HCID 178522562, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

6.3 g of 4-hydroxy-8-trifluoromethyl-quinoline-3-carboxylic acid chloride were added with stirring under an inert gas to 90 ml of pyridine and a solution of 2.35 g of 2-imino-2,3,4,5-tetrahydrothiazole in 15 ml of pyridine were added thereto. The mixture was stirred for 18 hours and was evaporated to dryness. The 11.5 g of residue were taken up in 40 ml of a 10% potassium carbonate solution and the solution was extracted with ethyl acetate. The combined organic phases were chromatographed over silica gel and the product was eluted with a 9-1 benzene-ethanol mixture. The elute was dried and the product was crystallized from ethanol to obtain 1.93 g of N-(4,5-dihydro-2-thiazolyl)-4-hydroxy-8-trifluoromethyl-quinoline-3-carboxamide melting at 267°-268° C.

Workup

  1. customwas evaporated to dryness
  2. extractionthe solution was extracted with ethyl acetate
  3. customThe combined organic phases were chromatographed over silica gel
  4. washthe product was eluted with a 9-1 benzene-ethanol mixture
  5. customThe elute was dried
  6. customthe product was crystallized from ethanol

Sources & evidence

ORD record
ord-451f88f0559d47bbbaeb516e472dce51
Source dataset
uspto-grants-1978_08
Patent number
US04107310

Reaction notes

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