Dimethylformamide → 4,9-Dihydro-9-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 1606454Notes

Reaction equation

HRID 1606454 reaction equation
[CH:1]1[S:2][CH:3]=[C:4]2[C:10]=1[C:9](=[O:11])[NH:8][C:7]1[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=1[NH:5]2.[H-].[Na+].[CH3:18]N(C)C=O.CI>O>[CH3:18][N:8]1[C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[NH:5][C:4]2=[CH:3][S:2][CH:1]=[C:10]2[C:9]1=[O:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 125216414,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 203922504,9-Dihydro-9-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 0.84 g. of 4,9-dihydro-10H-thieno[3,4-b] [1,5]benzodiazepin-10-one and 0.18 g. of 55% sodium hydride-mineral oil dispersion in 25 ml. of dimethylformamide is added 0.3 ml. of methyl iodide. The reaction mixture is stirred for 2.5 hours, cooled, diluted with water and filtered. The solid product is recrystallized from methanol-water to give pale yellow crystals, m.p. 195°-198°C.

Workup

  1. additionTo a stirred mixture of 0.84 g
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe solid product is recrystallized from methanol-water
  5. customto give pale yellow crystals, m.p. 195°-198°C.

Sources & evidence

ORD record
ord-6f1da6f332014a05a4ee306c711d68fb
Source dataset
uspto-grants-1976_04
Patent number
US03953430

Reaction notes

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