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

HRID 1606439Notes

Reaction equation

HRID 1606439 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-08e7da88d4564f1497958b0b922bf579
Source dataset
uspto-grants-1976_04
Patent number
US03953430

Reaction notes

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