Sodium hydride → 4,9-Dihydro-9-(2-dimethylaminoathyl)-4-methyl-thieno[3,4-b][1,5]benzodiazepin-10-on

HRID 436132Notes

Reaction equation

HRID 436132 reaction equation
[H-].[Na+].Cl.[CH3:4][N:5]([CH3:9])[CH2:6][CH2:7]Cl.[CH3:10][N:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][C:14](=[O:22])[C:13]2=[CH:23][S:24][CH:25]=[C:12]12>CN(C)C=O>[CH3:4][N:5]([CH3:9])[CH2:6][CH2:7][N:15]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:11]([CH3:10])[C:12]2=[CH:25][S:24][CH:23]=[C:13]2[C:14]1=[O:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 125216424,9-Dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 214552354,9-Dihydro-9-(2-dimethylaminoathyl)-4-methyl-thieno[3,4-b][1,5]benzodiazepin-10-on

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.4 g. of 55% sodium hydride-mineral oil dispersion 0.5 g. of 2-dimethylaminoethylchloride hydrochloride and 25 ml. of dry dimethylformamide is stirred at room temperature for 0.5 hours. To the mixture is added 0.4 g. of 4,9-dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and stirring at room temperature is continued for 18 hours. The reaction mixture is cooled, quenched with water, acidified, decolorized and filtered. The filtrate is made alkaline and extracted with chloroform. The dried chloroform extracts are concentrated to give a solid which is recrystallized from chloroform-hexane to give off-white crystals, m.p. 147°-149° C.

Workup

  1. additionA mixture of 0.4 g
  2. additionTo the mixture is added 0.4 g
  3. temperatureThe reaction mixture is cooled
  4. customquenched with water
  5. filtrationfiltered
  6. extractionextracted with chloroform
  7. concentrationThe dried chloroform extracts are concentrated
  8. customto give a solid which
  9. customis recrystallized from chloroform-hexane
  10. customto give off-white crystals, m.p. 147°-149° C.

Sources & evidence

ORD record
ord-c9e7d6ef85e841e3adf6f9cc812d07ff
Source dataset
uspto-grants-1977_02
Patent number
US04007272

Reaction notes

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