Sulfuric Acid → Alprazolam

HRID 867067

Reaction equation

HRID 867067 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][NH2:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1.[C:21]([O-])([O-])(OCC)[CH3:22].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:21]([CH3:22])=[N:13][N:12]=[C:10]3[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 123908747-Chloro-2-hydrazinyl-5-phenyl-3H-1,4-benzodiazepineHCID 86598186Ethyl ortho-acetate

Product 1

HCID 2118Alprazolam

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2.84 parts of 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine in a mixture of 100 parts by volume of ethanol and 5 parts by volume of ethyl orthoacetate is added 1 part of concentrated sulfuric acid with stirring. The mixture is further stirred for 30 minutes, and about 100 parts by volume of a saturated aqueous sodium bicarbonate solution is added. The mixture is concentrated under reduced pressure. The resulting crystals are collected by filtration, washed with water and dried to give 8-chloro-1-methyl-6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine as colorless crystals. Recrystallization from acetone-n-hexane gives colorless needles melting at 226°-227° C.

Workup

  1. stirringThe mixture is further stirred for 30 minutes
  2. concentrationThe mixture is concentrated under reduced pressure
  3. filtrationThe resulting crystals are collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-7191ab0e30e746728ee43581e9355792
Source dataset
uspto-grants-1978_07
Patent number
US04102881

Linked notes

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