Methyl iodide → HCID 23336521, compound

HRID 903562Notes

Reaction equation

HRID 903562 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([SH:14])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].[CH3:15][O-].[Na+].IC>CO>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([S:14][CH3:15])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 126069591-(3,4-Dihydro-7-mercapto-2(1H)-isoquinolinyl)ethanone

Product 1

HCID 23336521HCID 23336521, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A suspension of N-acetyl-7-mercapto-1,2,3,4-tetrahydroisoquinoline (1.0 gm., 0.0048 m.) in 20 ml. of methanol was stirred in a nitrogen atmosphere. Sodium methoxide (0.3 gm., 0.0055 m.) and 5 ml. of iodomethane were added to the suspension. The mixture was stirred at 25° C. for thirty minutes, evaporated and partitioned between chloroform and water. The chloroform layer was washed, dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel, eluted with ethyl acetate to give pure N-acetyl-7-methylthio-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. customevaporated
  2. custompartitioned between chloroform and water
  3. washThe chloroform layer was washed
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-472fcd7da62c48eab446eb4ef1038c29
Source dataset
uspto-grants-1980_10
Patent number
US04228170

Reaction notes

Loading…