Sodium Bicarbonate → Alprazolam

HRID 1764517Notes

Reaction equation

HRID 1764517 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.Cl.[C:22](=N)(OCC)[CH3:23].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:22]([CH3:23])=[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

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 123908747-Chloro-2-hydrazinyl-5-phenyl-3H-1,4-benzodiazepine

Product 1

HCID 2118Alprazolam

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2.84 parts of 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine in 60 parts by volume of chloroform is added 2.46 parts of ethyl acetoimidate hydrochloride. The mixture is stirred for 8 hours, and then aqueous sodium bicarbonate is added so as to neutralize the mixture. The chloroform layer is separated, washed with water and dried over anhydrous sodium sulfate, followed by evaporation of the solvent. The residue is recrystallized from ethyl acetate to give 8-chloro-1-methyl-6-phenyl-4H-s-triazolo [4,3-a] [1,4] benzodiazepine as colorless needles. Melting point: 225° C to 226° C.

Workup

  1. customThe chloroform layer is separated
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customfollowed by evaporation of the solvent
  5. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-edb84fb3bd5e40d5a4c6820b21f0c60d
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

Loading…