Sodium hydride → HCID 21455248, compound

HRID 436136Notes

Reaction equation

HRID 436136 reaction equation
[H-].[Na+].Cl.Cl[CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[CH3:12][N:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[NH:17][C:16](=[O:24])[C:15]2=[CH:25][S:26][CH:27]=[C:14]12>CN(C)C=O>[CH3:12][N:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]([CH2:5][CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[C:16](=[O:24])[C:15]2=[CH:25][S:26][CH:27]=[C:14]12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 125216424,9-Dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 21455248HCID 21455248, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.31 g. of 55% sodium hydride-mineral oil dispersion and 0.60 g. of N-(2-chloroethyl)pyrrolidine hydrochloride in 25 ml. of dry dimethylformamide is stirred at room temperature for 0.5 hours. To the mixture is added 0.40 g. of 4,9-dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and stirring is continued for 18 hours. The reaction mixture is cooled, quenched with water, and extracted with chloroform. The dried chloroform extracts are concentrated to an oil which crystallizes on trituration with ether. Recrystallization from ethyl acetate-hexane gives white crystals, m.p. 139°-141° C.

Workup

  1. additionA mixture of 0.31 g
  2. additionTo the mixture is added 0.40 g
  3. temperatureThe reaction mixture is cooled
  4. customquenched with water
  5. extractionextracted with chloroform
  6. concentrationThe dried chloroform extracts are concentrated to an oil which
  7. customcrystallizes on trituration with ether
  8. customRecrystallization from ethyl acetate-hexane
  9. customgives white crystals, m.p. 139°-141° C.

Sources & evidence

ORD record
ord-39eef77769c1413e9dc57de04366871e
Source dataset
uspto-grants-1977_02
Patent number
US04007272

Reaction notes

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