Methyl iodide → HCID 21849679, compound

HRID 617745Notes

Reaction equation

HRID 617745 reaction equation
[O:1]=[C:2]1[NH:16][CH2:15][CH2:14][C:5]2([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][CH2:6]2)[CH2:4][CH2:3]1.[H-].[Na+].I[CH3:20]>CN(C=O)C.C(OCC)(=O)C>[CH3:20][N:16]1[C:2](=[O:1])[CH2:3][CH2:4][C:5]2([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][CH2:6]2)[CH2:14][CH2:15]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21849673HCID 21849673, compound

Product 1

HCID 21849679HCID 21849679, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1,2,3,5,6,7-Hexahydro-7-oxospiro[4H-azepine-4,3'(2H)-benzofuran] (D25, 0.42 g, 1.9 mmol) was dissolved in dry DMF (10 ml) and added under Ar to sodium hydride (80% in mineral oil, 0.09 g, 3 mmol) in dry DMF (1 ml). After stirring for 5 min, iodomethane (0.24 ml, 3.8 mmol) was added. The mixture was stirred for 1 h, diluted with ethyl acetate (150 ml), washed with water and brine, dried (Na2SO4) and evaporated to give the title compound (0.36 g, 79%) as yellow semi-solid.

Workup

  1. stirringThe mixture was stirred for 1 h
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-49064ffaa9144a94a08a21612caecf79
Source dataset
uspto-grants-1999_09
Patent number
US05952325

Reaction notes

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