Sodium hydride → HCID 21455248, compound

HRID 1606444Notes

Reaction equation

HRID 1606444 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-19d06028d70648ca9fb20d8994ec41bc
Source dataset
uspto-grants-1976_04
Patent number
US03953430

Reaction notes

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