Sodium hydride → HCID 11419968, compound

HRID 1296550Notes

Reaction equation

HRID 1296550 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]=[N:4]1.Cl[CH2:20][C:21]1[N:22]=[C:23]([CH:26]=[CH:27][C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[O:24][CH:25]=1>CN(C)C=O>[F:37][C:34]([F:35])([F:36])[C:30]1[CH:29]=[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]([CH2:11][CH2:10][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:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 121094944-(4-[1,2,3]Triazol-1-yl-butyl)phenolHCID 69421536HCID 69421536, compound

Product 1

HCID 11419968HCID 11419968, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

26 mg (1.0 mmol) of 95% sodium hydride were given at 0° C. to a solution of 217 mg (1.00 mmol) 4-(4-[1,2,3]triazol-1-yl-butyl)-phenol in 6.0 ml N,N-dimethylformamide and stirred for 30 min. 288 mg (1.00 mmol) 4-Chloromethyl-2-[2-(3-trifluoromethyl-phenyl)-vinyl]-oxazole dissolved in 1.0 ml N,N-dimethylformamide were added at 0° C., stirring continued at 0° C. for 1 h and 12 h at room temperature thereafter. The mixture was quenched by 30 ml water, stirred for 1 h and the precipitate isolated by filtration. After washing with water, three times with cold ether and drying at 40° C. in vacuo, 192 mg (41%) 1-[4-(4-{2-[2-(E)-(3-Trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1H-[1,2,3]triazole were obtained.

Workup

  1. additionwere added at 0° C.
  2. stirringstirring
  3. waitcontinued at 0° C. for 1 h and 12 h at room temperature
  4. customThe mixture was quenched by 30 ml water
  5. stirringstirred for 1 h
  6. customthe precipitate isolated by filtration
  7. washAfter washing with water, three times with cold ether
  8. customdrying at 40° C. in vacuo

Sources & evidence

ORD record
ord-6c2434f14cbd4777bbb76f5492fcc2c3
Source dataset
uspto-grants-2007_07
Patent number
US07247649B2

Reaction notes

Loading…