Dimethyl Sulfoxide → 4,9-Dihydro-4-(2-dimethylaminoethyl)-9-methyl-10H-thieno[3,4-b] [1,5]benzodiazepin-10-one

HRID 436147Notes

Reaction equation

HRID 436147 reaction equation
[H-].[Na+].Cl.[CH3:4][N:5]([CH2:7][CH2:8]Cl)[CH3:6].CS(C)=O.[CH3:14][N:15]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[NH:19][C:18]2=[CH:26][S:27][CH:28]=[C:17]2[C:16]1=[O:29]>Cl.CCOCC>[CH3:4][N:5]([CH3:6])[CH2:7][CH2:8][N:19]1[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:15]([CH3:14])[C:16](=[O:29])[C:17]2=[CH:28][S:27][CH:26]=[C:18]12

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 203922504,9-Dihydro-9-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 214552594,9-Dihydro-4-(2-dimethylaminoethyl)-9-methyl-10H-thieno[3,4-b] [1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.72 g. of 55% sodium hydride-mineral oil dispersion and 0.60 g. of dimethylaminoethylchloride hydrochloride in 25 ml. of dimethylsulfoxide is stirred at room temperature for 0.5 hours. To the mixture is added 0.46 g. of 4,9-dihydro-9-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and stirring is continued for 3 hours. The reaction mixture is quenched by dropwise addition of water, diluted with about 200 ml. of water, acidified, filtered, made alkaline with 5N sodium hydroxide and extracted several times with chloroform. The chloroform extracts are dried over magnesium sulfate and concentrated under reduced pressure to give an amber oil. The oil is dissolved in a minimal volume of ethanolic hydrogen chloride solution and diluted with ether to give an oily semi-solid which slowly crystallizes. Recrystallization from ethanol-ether gives tan crystals, m.p. 245°-248° C. (dec.).

Workup

  1. additionA mixture of 0.72 g
  2. additionTo the mixture is added 0.46 g
  3. customThe reaction mixture is quenched by dropwise addition of water
  4. additiondiluted with about 200 ml
  5. filtrationfiltered
  6. extractionextracted several times with chloroform
  7. dry with materialThe chloroform extracts are dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give an amber oil
  10. customto give an oily semi-solid which
  11. customslowly crystallizes
  12. customRecrystallization from ethanol-ether
  13. customgives tan crystals, m.p. 245°-248° C. (dec.)

Sources & evidence

ORD record
ord-5fde88a483eb4610ae185cb7737f33fc
Source dataset
uspto-grants-1977_02
Patent number
US04007272

Reaction notes

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