Sodium hydride → 1-[2-(4-allyloxy-2-methyl-benzylsulfanyl)ethyl]-1H-[1,2,3]triazole

HRID 892259Notes

Reaction equation

HRID 892259 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][SH:12])=[C:7]([CH3:13])[CH:6]=1)[CH:2]=[CH2:3].[N:14]1([CH2:19][CH2:20]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:18]=[CH:17][N:16]=[N:15]1.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12][CH2:20][CH2:19][N:14]2[CH:18]=[CH:17][N:16]=[N:15]2)=[C:7]([CH3:13])[CH:6]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 22242072(4-Allyloxy-2-methyl-phenyl)-methanethiolHCID 226671112-(1H-1,2,3-triazol-1-yl)ethyl 4-methyl-1-benzenesulfonate

Product 1

HCID 222420831-[2-(4-allyloxy-2-methyl-benzylsulfanyl)ethyl]-1H-[1,2,3]triazoleYield 94.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 1.98 g (10.2 mmol) (4-allyloxy-2-methyl-phenyl)-methanethiol and 2.72 g (10.2 mmol) toluene-4-sulfonic acid 2-[1,2,3]triazol-1-yl-ethyl ester in 25 ml N,N-dimethylformamide was added under argon at −50° C. 515 mg (20.4 mmol) sodium hydride. The mixture was allowed to warm up to room temperature and was stirred under argon for 12 hours. 80% of the DMF was stilled off in vacuo, ethyl acetate and water given to the mixture. The aqueous phase was reextracted with ethyl acetate and the combined organic extracts dried and evaporated to yield 2.8 g of 1-[2-(4-allyloxy-2-methyl-benzylsulfanyl)ethyl]-1H-[1,2,3]triazole as brown oil. The raw material (73% purity) was used without further purification.

Workup

  1. additionwas added under argon at −50° C
  2. customthe combined organic extracts dried
  3. customevaporated

Sources & evidence

ORD record
ord-cd96bc8283bc4b05a80a37544652ec7f
Source dataset
uspto-grants-2006_02
Patent number
US07005526B2

Reaction notes

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