Water → HCID 11157095, compound

HRID 750968Notes

Reaction equation

HRID 750968 reaction equation
[H-].[Na+].[N:3]1([CH2:8][CH2:9][S:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[O:11])[CH:7]=[CH:6][N:5]=[N:4]1.Cl[CH2:21][C:22]1[N:23]=[C:24]([CH:27]=[CH:28][C:29]2[CH:34]=[CH:33][C:32]([S:35]([C:37]([F:40])([F:39])[F:38])=[O:36])=[CH:31][CH:30]=2)[O:25][CH:26]=1.O>CN(C=O)C>[F:40][C:37]([F:38])([F:39])[S:35]([C:32]1[CH:33]=[CH:34][C:29](/[CH:28]=[CH:27]/[C:24]2[O:25][CH:26]=[C:22]([CH2:21][O:19][C:16]3[CH:15]=[CH:14][C:13]([CH2:12][S:10]([CH2:9][CH2:8][N:3]4[CH:7]=[CH:6][N:5]=[N:4]4)=[O:11])=[CH:18][CH:17]=3)[N:23]=2)=[CH:30][CH:31]=1)=[O:36]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 222420754-(2-[1,2,3]Triazol-1-yl-ethanesulfinylmethyl)-phenolHCID 692923894-Chloromethyl-2-[2-(4-trifluoromethylsulfinyl-phenyl)-vinyl]-oxazole

Product 1

HCID 11157095HCID 11157095, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14 mg (0.55 mmol) 95% sodium hydride were given to a solution of 126 mg (0.50 mmol) 4-(2-[1,2,3]triazol-1-yl-ethanesulfinylmethyl)-phenol in 4.0 ml DMF and stirred for 15 min. 168 mg (0.50 mmol) 4-Chloromethyl-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazole were added and stirring continued at r.t. overnight. After addition of 6 ml water the resulting precipitate was collected and combined with additional material obtained by extraction of the aqueous phase at pH=3 with ethyl acetate, drying (sodium sulfate) and evaporation. Purification by chromatography on silica gel (eluent: ethyl acetate/methanol 9:1) gave 130 mg (77%) powder.

Workup

  1. stirringstirring
  2. waitcontinued at r.t. overnight
  3. customwas collected
  4. customobtained by extraction of the aqueous phase at pH=3 with ethyl acetate
  5. customdrying
  6. custom(sodium sulfate) and evaporation
  7. customPurification by chromatography on silica gel (eluent: ethyl acetate/methanol 9:1)

Sources & evidence

ORD record
ord-97ff784f237f4ace90ed2efdf1ada9b5
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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