Water → HCID 69003325, compound

HRID 1951606Notes

Reaction equation

HRID 1951606 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:29])[CH2:9][CH2:10][C:11]2[S:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)=[N:13][C:12]=2[CH:26]([CH3:28])[CH3:27])=[CH:4][CH:3]=1.[CH:30]1[CH:35]=[C:34]([N+:36]([O-:38])=[O:37])[C:33]([S:39](Cl)(=[O:41])=[O:40])=[CH:32][CH:31]=1.O>N1C=CC=CC=1>[CH:26]([C:12]1[N:13]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[S:15][C:11]=1[CH2:10][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:39]([C:33]2[CH:32]=[CH:31][CH:30]=[CH:35][C:34]=2[N+:36]([O-:38])=[O:37])(=[O:40])=[O:41])=[CH:3][CH:4]=1)=[O:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 962WaterHCID 155402-Nitrobenzenesulfonyl chlorideHCID 69000454HCID 69000454, compound

Product 1

HCID 69003325HCID 69003325, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The obtained 1-(4-aminophenyl)-3-[4-isopropyl-2-[4-(trifluoromethyl)phenyl]thiazol-5-yl]-propan-1-one (250 mg, 0.597 mmol) was dissolved in anhydrous pyridine (5 mL). O-nitrophenylsulfonyl chloride (146 mg, 0.659 mmol) was added to the solution. The mixture was stirred at room temperature for 1 hour. The outer temperature was heated to 80° C., and the mixture was further stirred for 16 hours. The mixture was cooled to room temperature. Water was added to the mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine, and dried with anhydrous sodium sulfate to remove the solvent. The obtained residue was purified by silica gel column chromatography with hexane/ethyl acetate (8:2, v/v) to give the desired compound (265 mg) as yellow crystalline product (yield 74%).

Workup

  1. temperatureThe outer temperature was heated to 80° C.
  2. stirringthe mixture was further stirred for 16 hours
  3. temperatureThe mixture was cooled to room temperature
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. customto remove the solvent
  8. customThe obtained residue was purified by silica gel column chromatography with hexane/ethyl acetate (8:2, v/v)

Sources & evidence

ORD record
ord-c1f401c47115440d8560087fc8d75bc7
Source dataset
uspto-grants-2013_03
Patent number
US08404726B2

Reaction notes

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