Water → 1-[4-(4-{2-[2-(4-Pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-but-3-enyl]-1H-[1,2,3]triazole

HRID 1768073Notes

Reaction equation

HRID 1768073 reaction equation
[H-].[Na+].[N:3]1([CH2:8][CH2:9][CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH:7]=[CH:6][N:5]=[N: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>[F:37][S:34]([F:35])([F:36])([F:38])([F:39])[C:31]1[CH:32]=[CH:33][C:28]([CH:27]=[CH:26][C:23]2[O:24][CH:25]=[C:21]([CH2:20][O:18][C:15]3[CH:14]=[CH:13][C:12]([CH:11]=[CH:10][CH2:9][CH2:8][N:3]4[CH:7]=[CH:6][N:5]=[N:4]4)=[CH:17][CH:16]=3)[N:22]=2)=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 692918004-(4-[1,2,3]Triazol-1-yl-but-1-enyl)-phenolHCID 865985174-Chloromethyl-2-[2-(4-pentafluorosulfanyl-phenyl)-vinyl]-oxazole

Product 1

HCID 728270081-[4-(4-{2-[2-(4-Pentafluorosulfanyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-but-3-enyl]-1H-[1,2,3]triazoleYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

13 mg (0.50 mmol) 95% sodium hydride were given to a solution of 108 mg (0.50 mmol) 4-(4-[1,2,3]triazol-1-yl-but-1-enyl)-phenol in 4.0 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 10 ml water the resulting precipitate was collected, washed with water (2×10 ml), methanol (2×10 ml), diethyl ether and dried in vacuum at 40° C. to yield 225 mg (86%) of product.

Workup

  1. stirringstirring
  2. waitcontinued at r.t. overnight
  3. customwas collected
  4. washwashed with water (2×10 ml), methanol (2×10 ml), diethyl ether
  5. customdried in vacuum at 40° C.

Sources & evidence

ORD record
ord-b30638720d6b44838b5c362554cd483d
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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