Methyl iodide → HCID 21490959, compound

HRID 1973908Notes

Reaction equation

HRID 1973908 reaction equation
[OH:1][CH:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([CH2:11][C:12]([NH2:14])=[O:13])[CH2:4][CH2:3]1.[CH3:15]I>O1CCCC1.[Ag]=O>[CH3:15][O:1][CH:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]([CH2:11][C:12]([NH2:14])=[O:13])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 23347797HCID 23347797, compound

Product 1

HCID 21490959HCID 21490959, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Eight g (37.86 mm) of 4,5,6,7-tetrahydro-7-hydroxybenzo[b]thien-4-ylacetamide and methyl iodide (28 ml, 0.45 M) are stirred in tetrahydrofuran (160 ml). The suspension is treated with silver oxide (60 g, 0.259 M) added in portions over a period of 5 hours. The reaction mixture is stirred overnight, filtered through celite, the cake is washed with tetrahydrofuran (2 × 100 ml) and dichloromethane (100 ml) and the filtrate evaporated to afford the crude title compound as a yellow-orange solid (8.1 g, 95% Y) m.p. 108° C-113° C dec. Two recrystallizations from acetone/hexane afford the analytical specimen, m.p. 124° C-126° C dec.

Workup

  1. additionadded in portions over a period of 5 hours
  2. filtrationfiltered through celite
  3. washthe cake is washed with tetrahydrofuran (2 × 100 ml) and dichloromethane (100 ml)
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-7d0cfd67fae6463ba7d06700e9be7bb5
Source dataset
uspto-grants-1976_12
Patent number
US03998959

Reaction notes

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