Sulfuric Acid → HCID 86736041, compound

HRID 1764534Notes

Reaction equation

HRID 1764534 reaction equation
[NH:1]([C:3]1[CH2:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]2[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:5]=2[N:4]=1)[NH2:2].[CH:21]([O-])([O-])OCC.S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:20][C:17]1[CH:18]=[CH:19][C:5]2[N:4]3[CH:21]=[N:2][N:1]=[C:3]3[CH2:9][N:8]=[C:7]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:6]=2[CH:16]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 12570863HCID 12570863, compoundHCID 53630039Ethylorthoformate

Product 1

HCID 86736041HCID 86736041, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 5.3 parts of 2-hydrazino-7-methyl-5-phenyl-3H-1,4-benzodiazepine prepared in Example 5, 14.8 parts of ethyl orthoformate and 150 parts by volume of ethanol, is added dropwise 4 parts of fconcentrated sulfuric acid under cooling. The whole mixture is stirred for about 30 minutes and neutralized with a saturated aqueous solution of sodium bicarbonate, followed by extraction with chloroform. The chloroform layer is washed with water and dried over sodium sulfate. After evaporation of the solvent, the residue is treated with n-hexane, whereby 8-methyl-6-phenyl-4H-s-triazolo [4,3-a][1,4] benzodiazepine is yielded as crystals. Recrystallization from ethyl acetate yields pale yellow prisms melting at 177° C to 178° C.

Workup

  1. temperatureunder cooling
  2. extractionfollowed by extraction with chloroform
  3. washThe chloroform layer is washed with water
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvent
  6. additionthe residue is treated with n-hexane

Sources & evidence

ORD record
ord-593ada095ea5406c836325a0b8de6abe
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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