Water → 8-Methoxy-3-methyl-6-phenyl-11H-imidazo[1,2-c][2,3]benzodiazepine

HRID 1359579Notes

Reaction equation

HRID 1359579 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[CH2:7][C:8](=S)[NH:9][N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[CH:4]=1.CCOCCO.[NH2:27][CH2:28][C:29]1([CH3:34])OCCO1.O>COCCO>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[CH2:7][C:8]3[N:9]([C:29]([CH3:34])=[CH:28][N:27]=3)[N:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8076Glycol monoethyl etherHCID 12434663(2-Methyl-1,3-dioxolan-2-yl)methanamineHCID 178878218-methoxy-1-phenyl-4,5-dihydro-3H-2,3-benzodiazepine-4-thione

Product 1

HCID 181831588-Methoxy-3-methyl-6-phenyl-11H-imidazo[1,2-c][2,3]benzodiazepine

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

500 mg of 8-methoxy-1-phenyl-4,5-dihydro-3H-2,3-benzodiazepine-4-thione is stirred in 1.5 ml of ethylene glycol monomethyl ether (Cellosolve® and 548 mg of 2-aminomethyl-2-methyl-1,3-dioxolane while argon is passing through it for 10 hours at 60° C. After filtration and washing with cold ethanol and diisopropyl ether, 550 mg of imino compound, which is dissolved in 10 ml of ethanol, mixed with 10 ml of concentrated hydrocholoric acid and refluxed for 3 hours, is obtained. It is added to water, set at pH 11 and extracted with ethyl acetate. The ethyl acetate phase is washed with water, dried, filtered and concentrated by evaporation. After recrystallization from ethyl acetate/diisopropyl ether, 240 mg of 8-methoxy-3-methy-6-phenyl-11H-imidazo[1,2-c][2,3]benzodiazepine with a melting point of 140° C. is obtained.

Workup

  1. filtrationAfter filtration
  2. washwashing with cold ethanol and diisopropyl ether, 550 mg of imino compound, which
  3. dissolutionis dissolved in 10 ml of ethanol
  4. additionmixed with 10 ml of concentrated hydrocholoric acid
  5. temperaturerefluxed for 3 hours
  6. customis obtained
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate phase is washed with water
  9. customdried
  10. filtrationfiltered
  11. concentrationconcentrated by evaporation
  12. customAfter recrystallization from ethyl acetate/diisopropyl ether, 240 mg of 8-methoxy-3-methy-6-phenyl-11H-imidazo[1,2-c][2,3]benzodiazepine with a melting point of 140° C.
  13. customis obtained

Sources & evidence

ORD record
ord-22bfcb145d40480ea618676e756e34d0
Source dataset
uspto-grants-2003_07
Patent number
US06600036B2

Reaction notes

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