Acetone → HCID 21350774, compound

HRID 1359567Notes

Reaction equation

HRID 1359567 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:9][C:8]2[CH:10]=[C:11]3[O:16][CH2:15][O:14][C:12]3=[CH:13][C:7]=2[C:6]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[N:5][NH:4]1.Cl.[CH3:27][C:28]([CH3:30])=O>>[CH3:27][C:28]1([CH3:30])[N:4]2[N:5]=[C:6]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=3)[C:7]3[CH:13]=[C:12]4[O:14][CH2:15][O:16][C:11]4=[CH:10][C:8]=3[CH2:9][CH:3]2[CH2:2][O:1]1

Participants

4

Reactant 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 18183107HCID 18183107, compound

Product 1

HCID 21350774HCID 21350774, compound

Procedure

1.87 g (5.48 mmol) of 8-hydroxymethyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine is dissolved in 25 ml of acetone and mixed with 0.54 ml (6.67 mmol) of 37% HCl. After 30 minutes, the reaction mixture is cooled, and the hydrochloride is filtered off. The dichloromethane suspension of this salt is shaken with 20 ml of 8% NaHCO3 solution until the salt is dissolved. The organic phase is separated, washed with water, dried and concentrated by evaporation. After recrystallization, 1.7 g (81%) of the title compound, melting point 171-173° C., is obtained.

Workup

  1. temperaturethe reaction mixture is cooled
  2. filtrationthe hydrochloride is filtered off
  3. additionThe dichloromethane suspension of this salt
  4. dissolutionis dissolved
  5. customThe organic phase is separated
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated by evaporation
  9. customAfter recrystallization, 1.7 g (81%) of the title compound, melting point 171-173° C.
  10. customis obtained

Sources & evidence

ORD record
ord-d73431646df44271bf7f7f7111d332f1
Source dataset
uspto-grants-2003_07
Patent number
US06600036B2

Reaction notes

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