Sodium hydride → [4-(4-[1,2,3]Triazol-1-yl-but-1-enyl)-phenyl]-{2-[2-(4-trifluoromethane-sulfinyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-carbamic acid tert-butyl ester

HRID 1271440Notes

Reaction equation

HRID 1271440 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[CH:15][CH2:16][CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[N:19]2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:27][C:28]1[N:29]=[C:30]([CH:33]=[CH:34][C:35]2[CH:40]=[CH:39][C:38]([S:41]([C:43]([F:46])([F:45])[F:44])=[O:42])=[CH:37][CH:36]=2)[O:31][CH:32]=1>CN(C)C=O>[C:1]([O:5][C:6](=[O:23])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[CH:15][CH2:16][CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[N:19]2)=[CH:10][CH:9]=1)[CH2:27][C:28]1[N:29]=[C:30]([CH:33]=[CH:34][C:35]2[CH:36]=[CH:37][C:38]([S:41]([C:43]([F:46])([F:44])[F:45])=[O:42])=[CH:39][CH:40]=2)[O:31][CH:32]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 692923894-Chloromethyl-2-[2-(4-trifluoromethylsulfinyl-phenyl)-vinyl]-oxazoleHCID 69490216[4-(4-[1,2,3]Triazol-1-yl-but-1-enyl)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 69489717[4-(4-[1,2,3]Triazol-1-yl-but-1-enyl)-phenyl]-{2-[2-(4-trifluoromethane-sulfinyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-carbamic acid tert-butyl esterYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [4-(4-[1,2,3]triazol-1-yl-but-1-enyl)-phenyl]-carbamic acid tert-butyl ester (0.157 g, 0.5 mmol) in N,N-dimethyl formamide (4 ml) was treated with sodium hydride (0.014 g, 0.5 mmol) and stirred for 30 min at room temperature. After addition of 4-chloromethyl-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazole (0.168 g, 0.5 mmol) and stirring for 12 h the reaction was quenched by the addition of a sat. NH4Cl solution (8 ml). Extraction with ethyl acetate (3×10 ml), washing with water, drying over sodium sulfate and concentration in vacuo yields crude [4-(4-[1,2,3]triazol-1-yl-but-1-enyl)-phenyl]-{2-[2-(4-trifluoromethane-sulfinyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-carbamic acid tert-butyl ester (0.28 g) which was used in the next step without any further purification.

Workup

  1. stirringstirring for 12 h the reaction
  2. customwas quenched by the addition of a sat. NH4Cl solution (8 ml)
  3. extractionExtraction with ethyl acetate (3×10 ml)
  4. washwashing with water
  5. dry with materialdrying over sodium sulfate and concentration in vacuo

Sources & evidence

ORD record
ord-82661148720549cdbb309e3d4236078c
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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