Water → HCID 11387413, compound

HRID 1768069Notes

Reaction equation

HRID 1768069 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]([F:40])([F:39])([F:38])([F:37])[F:36])=[CH:31][CH:30]=2)[O:25][CH:26]=1.O>CN(C=O)C>[F:38][S:35]([F:36])([F:37])([F:39])([F:40])[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

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 222420754-(2-[1,2,3]Triazol-1-yl-ethanesulfinylmethyl)-phenolHCID 865985174-Chloromethyl-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole

Product 1

HCID 11387413HCID 11387413, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

14 mg (0.50 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 3.0 ml DMF and stirred for 15 min. 173 mg (0.50 mmol) 4-chloromethyl-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole were added and stirring continued at r.t. overnight. After addition of 6 ml water the resulting precipitate was washed with water (2×), water/methanol 1:1 (2×), ethyl acetate/n-heptane 3:1 (1×), little ethyl acetate (1×), diethyl ether (1×) and dried in vacuum at 40° C. Further purification by chromatography on silica gel (eluent:ethyl acetate/methanol 15:1) and stirring of the isolated product with little ether and ethyl acetate and drying gave 48 mg (17%) white powder.

Workup

  1. stirringstirring
  2. waitcontinued at r.t. overnight
  3. washwas washed with water (2×), water/methanol 1:1 (2×), ethyl acetate/n-heptane 3:1 (1×), little ethyl acetate (1×), diethyl ether (1×)
  4. customdried in vacuum at 40° C
  5. customFurther purification by chromatography on silica gel (eluent:ethyl acetate/methanol 15:1)
  6. stirringstirring of the isolated product with little ether and ethyl acetate
  7. customdrying

Sources & evidence

ORD record
ord-645d2a0d8af247e6a4c745bf68c69b0b
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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