Sodium hydride → HCID 11816030, compound

HRID 842538Notes

Reaction equation

HRID 842538 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].C1(C)C=C(C)C=C(C)C=1S(O[NH2:26])(=O)=O>O1CCCC1>[NH2:26][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=2)[CH:7]=[CH:8]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 766596-Methoxy-1H-indoleHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine

Product 1

HCID 11816030HCID 11816030, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A mixture of 0.735 g 6-methoxyindole and 5 ml tetrahydrofuran (THF) is added to a suspension of 0.44 g of 60% sodium hydride in 10 ml THF at 0° C. After 15 minutes a mixture 1.07 g O-mesitylsulfonyl-hydroxylamine and 15 ml THF is added. Stirring at 0° C. is continued for 1.5 hours. The mixture is poured into ice cold water, extracted with ethyl acetate, and purified by flash chromatography.

Workup

  1. additionThe mixture is poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c17f8959d054479f94fb192877502069
Source dataset
uspto-grants-2002_04
Patent number
US06376426B1

Reaction notes

Loading…