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

HRID 892249Notes

Reaction equation

HRID 892249 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][SH:12])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].[N:13]1([CH2:18][CH2:19]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:17]=[CH:16][N:15]=[N:14]1.[H-].[Na+]>CN(C)C=O>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12][CH2:19][CH2:18][N:13]2[CH:17]=[CH:16][N:15]=[N:14]2)=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 22242087[4-(Prop-2-en-1-yloxy)phenyl]methanethiolHCID 226671112-(1H-1,2,3-triazol-1-yl)ethyl 4-methyl-1-benzenesulfonate

Product 1

HCID 222420761-[2-(4-Allyloxy-benzylsulfanyl)-ethyl]-1H-[1,2,3]triazoleYield 86.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 13.0 g (50.5 mmol) (4-allyloxy-phenyl)-methanethiol and 13.5 g (50.5 mmol) toluene-4-sulfonic acid 2-[1,2,3]triazol-1-yl-ethyl ester in 125 ml N,N-dimethylformamide was added under argon at −30° C. 2.42 g (101 mmol) sodium hydride. The mixture was allowed to warm up to room temperature and was stirred under argon for 12 hours. After quenching with 100 ml water, the mixture was diluted with dichloromethane, washed with water, dried and evaporated. Purification on silica after elution with ethyl acetate/heptane 1:1 yielded 12.0 g (86%) 1-[2-(4-allyloxy-benzylsulfanyl)-ethyl]-1H[1,2,3]triazole as slightly yellow oil.

Workup

  1. additionwas added under argon at −30° C
  2. customAfter quenching with 100 ml water
  3. additionthe mixture was diluted with dichloromethane
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customPurification on silica
  8. washafter elution with ethyl acetate/heptane 1:1

Sources & evidence

ORD record
ord-5b92bcc172224683915bc72e6ea5135a
Source dataset
uspto-grants-2006_02
Patent number
US07005526B2

Reaction notes

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