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

HRID 1606446Notes

Reaction equation

HRID 1606446 reaction equation
[H-].[Na+].Cl.Cl[CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[CH3:13][N:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[NH:18][C:17](=[O:25])[C:16]2=[CH:26][S:27][CH:28]=[C:15]12>CN(C)C=O>[CH3:13][N:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]([CH2:5][CH2:6][N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[C:17](=[O:25])[C:16]2=[CH:26][S:27][CH:28]=[C:15]12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 125216424,9-Dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 215430714,9-Dihydro-4-methyl-9-(2-morpholinoethyl)-10H-thieno[3,4-b] [1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.31 g. of 55% sodium hydride-mineral oil dispersion and 0.65 g. of N-(2-chloroethyl)morpholine 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 dryness and the solid residue is recrystallized from ethyl acetate-hexane to give white crystals, m.p. 109°-111°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 dryness
  7. customthe solid residue is recrystallized from ethyl acetate-hexane
  8. customto give white crystals, m.p. 109°-111°C.

Sources & evidence

ORD record
ord-7468823c764e465fb00068d248105e3d
Source dataset
uspto-grants-1976_04
Patent number
US03953430

Reaction notes

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