Methyl iodide → 5-Methylthiopyrano[3,2-b]indol-4(5H)-one

HRID 918477Notes

Reaction equation

HRID 918477 reaction equation
[H-].[Na+].[S:3]1[C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:7]=2[C:6](=[O:16])[CH:5]=[CH:4]1.[CH3:17]I>CCCCCC.CN(C)C=O>[CH3:17][N:8]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=2[C:15]2[S:3][CH:4]=[CH:5][C:6](=[O:16])[C:7]1=2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20326608Thiopyrano[3,2-b]indol-4(5H)-one

Product 1

HCID 203266115-Methylthiopyrano[3,2-b]indol-4(5H)-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

Sodium hydride (2.3 g of 50% suspension in mineral oil, 0.05 mole) is washed with hexane and suspended in 25 ml of dimethylformamide (DMF). Thiopyrano [3,2-b] indol-4(5H)-one, 10.0 g (0.05 mole) in 130 ml of DMF is added and the mixture stirred for 3 hours. Methyl iodide (14.2 g, 0.1 mole) is added and the mixture stirred for 3 hours and then poured over ice. The white precipitate is filtered, dried and recrystallized from hexane to give 9.3 g of product, mp 113°-114°C.

Workup

  1. stirringthe mixture stirred for 3 hours
  2. additionpoured over ice
  3. filtrationThe white precipitate is filtered
  4. customdried
  5. customrecrystallized from hexane

Sources & evidence

ORD record
ord-9df573f6758b4ff6acfc3a5a18dc6c20
Source dataset
uspto-grants-1976_07
Patent number
US03971806

Reaction notes

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