Sulfuric Acid → HCID 20317274, compound

HRID 867068Notes

Reaction equation

HRID 867068 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][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:6]=2[CH:22]=1.[CH:23]([O-])([O-])OCC.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[CH:23]=[N:13][N:12]=[C:10]3[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:6]=2[CH:22]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 22768408HCID 22768408, compoundHCID 53630039Ethylorthoformate

Product 1

HCID 20317274HCID 20317274, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.6 parts of 7-chloro-2-hydrazino-5-(4-methoxyphenyl)-3H-1,4-benzodiazepine in 50 parts by volume of ethanol is added 3 parts of ethyl orthoformate. To the mixture is added 0.5 part by volume of concentrated sulfuric acid with stirring. After 5 minutes, the reaction mixture is neutralized with a saturated aqueous sodium bicarbonate solution, followed by removal of the solvent. To the residue is added water, whereupon 8-chloro-6-(4-methoxyphenyl)-4H-s-triazolo[4,3-a][1,4]benzodiazepine is obtained as crystals. Recrystallization from acetone-ethyl acetate gives pale yellow flakes melting at 216°-217° C.

Workup

  1. customfollowed by removal of the solvent
  2. additionTo the residue is added water

Sources & evidence

ORD record
ord-6e87a2546942436f9ff3d7580fa0c1ac
Source dataset
uspto-grants-1978_07
Patent number
US04102881

Reaction notes

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