Sulfuric Acid → HCID 20317266, compound

HRID 1764530Notes

Reaction equation

HRID 1764530 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.[C:23]([O-])([O-])(OCC)[CH3:24].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:23]([CH3:24])=[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 86598186Ethyl ortho-acetate

Product 1

HCID 20317266HCID 20317266, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2.1 parts of 7-chloro-2-hydrazino-5-(p-methoxyphenyl)-3H-1,4-benzodiazepine, prepared in Example 2, 4.33 parts of ethyl orthoacetate and 60 parts by volume of ethanol is added dropwise 0.75 part by volume of concentrated sulfuric acid. The mixture is stirred for about 15 minutes. After completion of the reaction, the reaaction mixture is neutralized with a saturated aqueous solution of sodium bicarbonate, whereby 8-chloro-1-methyl-6-(p-methoxyphenyl)-4H-s-triazolo [4,3-a] [1,4] benzodiazepine is yielded as crystals. Recrystallization from a mixture of methanol and chloroform yields colorless needles melting at 268° C to 269° C.

Workup

  1. customAfter completion of the reaction

Sources & evidence

ORD record
ord-2c2bf3f32c734b32968e76a123e4cb28
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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