Water → 4-[4-(4-Imidazol-1-yl-butyl)-phenoxymethyl]-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole

HRID 1768041Notes

Reaction equation

HRID 1768041 reaction equation
[H-].[Na+].[N:3]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH:7]=[CH:6][N:5]=[CH:4]1.Cl[CH2:20][C:21]1[N:22]=[C:23]([CH:26]=[CH:27][C:28]2[CH:33]=[CH:32][C:31]([S:34]([F:39])([F:38])([F:37])([F:36])[F:35])=[CH:30][CH:29]=2)[O:24][CH:25]=1.O>CN(C=O)C>[N:3]1([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:20][C:21]3[N:22]=[C:23]([CH:26]=[CH:27][C:28]4[CH:29]=[CH:30][C:31]([S:34]([F:39])([F:35])([F:36])([F:37])[F:38])=[CH:32][CH:33]=4)[O:24][CH:25]=3)=[CH:16][CH:17]=2)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 220096641-[4-(4-Hydroxyphenyl)butyl]imidazoleHCID 865985174-Chloromethyl-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole

Product 1

HCID 729769504-[4-(4-Imidazol-1-yl-butyl)-phenoxymethyl]-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25.0 mg (0.100 mmol) 95% sodium hydride were given to a solution of 216 mg (0.100 mmol) 4-(4-[Imidazol-1-yl]-butyl)-phenol in 5.0 ml DMF and stirred for 15 min. 346 mg (0.100 mmol) 4-chloromethyl-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole were added and stirring continued overnight. After addition of 10 ml water the resulting precipitate was isolated and washed with 2×10 ml water, 2×10 ml methanol and with diethyl ether. Yield 411 mg (78%). MS: M=526.2 (ESI+)

Workup

  1. stirringstirring continued overnight
  2. customwas isolated
  3. washwashed with 2×10 ml water, 2×10 ml methanol and with diethyl ether

Sources & evidence

ORD record
ord-cbc8bfbb0b9b4c80b4da589b6e442bdc
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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