Potassium Carbonate → HCID 19101653, compound

HRID 1974508Notes

Reaction equation

HRID 1974508 reaction equation
[OH:1][C:2]([C:14]1[S:15][CH:16]=[CH:17][N:18]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1)[C:3]([F:6])([F:5])[F:4].Cl.Cl[CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:1][C:2]([C:14]1[S:15][CH:16]=[CH:17][N:18]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:21][C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=2)[CH:8]=1)[C:3]([F:5])([F:4])[F:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 19101630HCID 19101630, compound

Product 1

HCID 19101653HCID 19101653, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[1-hydroxy-1-(3-hydroxyphenyl)-2,2,2-trifluoroethyl]thiazole (0.33 g), 2-chloromethylquinoline hydrochloride (0.22 g), potassium carbonate (0.5 g) and dimethylformamide (5 ml) was stirred at ambient temperature for 24 hours. The mixture was partitioned between ethyl acetate and water and the organic layer was separated, washed with a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column chromatography eluting with chloroform/ethyl acetate (9/1 v/v) to give 2-[1-hydroxy-1-[3-(quinol-2-ylmethoxy)phenyl]-2,2,2-trifluoroethyl]thiazole (0.15 g, 30%), m.p. 177° C.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customthe organic layer was separated
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography
  7. washeluting with chloroform/ethyl acetate (9/1 v/v)

Sources & evidence

ORD record
ord-f93536b5036d49069d2f9c81a501ade0
Source dataset
uspto-grants-1994_02
Patent number
US05283245

Reaction notes

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