Sodium hydride → 5,10-Dihydro-5-(2-dimethylaminoethyl)-10-methyl-6H-pyrido[3,2-b]thieno[3,4-e][1,4]diazepin-6-one

HRID 436150Notes

Reaction equation

HRID 436150 reaction equation
[H-].[Na+].Cl.[CH3:4][N:5]([CH2:7][CH2:8]Cl)[CH3:6].[CH3:10][N:11]1[C:17]2=[CH:18][S:19][CH:20]=[C:16]2[C:15](=[O:21])[NH:14][C:13]2[CH:22]=[CH:23][CH:24]=[N:25][C:12]1=2>CN(C)C=O>[CH3:4][N:5]([CH3:6])[CH2:7][CH2:8][N:14]1[C:15](=[O:21])[C:16]2=[CH:20][S:19][CH:18]=[C:17]2[N:11]([CH3:10])[C:12]2[N:25]=[CH:24][CH:23]=[CH:22][C:13]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 127620225,10-dihydro-10-methyl-6H-pyrido[3,2-b]thieno[3,4-e][1,4]diazepin-6-one

Product 1

HCID 214552385,10-Dihydro-5-(2-dimethylaminoethyl)-10-methyl-6H-pyrido[3,2-b]thieno[3,4-e][1,4]diazepin-6-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.20 g. of 55% sodium hydride-mineral oil dispersion and 0.3 g. of dimethylaminoethylchloride hydrochloride in 12 ml. of dry dimethylformamide is stirred at room temperature for 0.5 hours. To the mixture is added 0.23 g. of 5,10-dihydro-10-methyl-6H-pyrido[3,2-b]thieno[3,4-e][1,4]diazepin-6-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 give an amber oil, which is crystallized from hexane to give an off-white solid, m.p. 129°-130° C.

Workup

  1. additionA mixture of 0.20 g
  2. additionTo the mixture is added 0.23 g
  3. temperatureThe reaction mixture is cooled
  4. customquenched with water
  5. extractionextracted with chloroform
  6. concentrationThe dried chloroform extracts are concentrated
  7. customto give an amber oil, which
  8. customis crystallized from hexane
  9. customto give an off-white solid, m.p. 129°-130° C.

Sources & evidence

ORD record
ord-a2eb074146c7406b805d5fac2eac3519
Source dataset
uspto-grants-1977_02
Patent number
US04007272

Reaction notes

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