Methyl iodide → 1-[2,3-Dihydro-5-(methylthio)-1H-indol-1-yl]ethanone

HRID 356017Notes

Reaction equation

HRID 356017 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([SH:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CI.[CH2:16](N(CC)CC)C>ClCCl>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13][CH3:16])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 10535785HCID 10535785, compound

Product 1

HCID 106559461-[2,3-Dihydro-5-(methylthio)-1H-indol-1-yl]ethanoneYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-acetyl-5-mercaptoindoline (D3) (0.98 g, 5.07 mmol), methyl iodide (0.35 ml, 5.6 mmol) and triethylamine (0.78 ml, 5.6 mmol) in dichloromethane (25 ml) was stirred for 18 h at room temperature. The mixture was evaporated, and the residue was redissolved in dichloromethane and washed with dilute hydrochloric acid. The organic solution was dried and evaporated to give the title compound (0.98 g, 93%).

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue was redissolved in dichloromethane
  3. washwashed with dilute hydrochloric acid
  4. customThe organic solution was dried
  5. customevaporated

Sources & evidence

ORD record
ord-bafeccf7209a4234b63c6054434ab550
Source dataset
uspto-grants-1998_11
Patent number
US05834494

Reaction notes

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