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

HRID 436146Notes

Reaction equation

HRID 436146 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-464a81f81d234e15b9bf668e99004aa4
Source dataset
uspto-grants-1977_02
Patent number
US04007272

Reaction notes

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