Sulfuric Acid → HCID 86736042, compound

HRID 1764536Notes

Reaction equation

HRID 1764536 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][NH2:13])[CH:9]([CH2:14][CH:15]([CH3:17])[CH3:16])[N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:24]=1.[CH:25](OCC)(OCC)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:25]=[N:13][N:12]=[C:10]3[CH:9]([CH2:14][CH:15]([CH3:17])[CH3:16])[N:8]=[C:7]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:6]=2[CH:24]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 22768404HCID 22768404, compound

Product 1

HCID 86736042HCID 86736042, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1.7 parts of 7-chloro-2-hydrazino-3-isobutyl-5-phenyl-3H-1,4-benzodiazepine prepared in Examples 8 and 11, 3.7 parts of triethyl orthoformate and 40 parts by volume of ethanol, is added 1 part of concentrated sulfuric acid with stirring and ice-cooling. The mixture is stirred for about 20 minutes at room temperature. After completion of reaction, the mixture is neutralized with 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-chloro-4-isobutyl-6-phenyl-4H-s-triazolo [4,3-a][1,4] benzodiazepine is yielded as pale yellow crystals. Recrystallization from a mixture of benzene and n-hexane yields colorless needles melting at 140.5° C to 141.5° C.

Workup

  1. temperatureice-cooling
  2. stirringThe mixture is stirred for about 20 minutes at room temperature
  3. customAfter completion of reaction
  4. extractionfollowed by extraction with chloroform
  5. washThe chloroform layer is washed with water
  6. dry with materialdried over sodium sulfate
  7. customAfter evaporation of the solvent
  8. additionthe residue is treated with n-hexane

Sources & evidence

ORD record
ord-a80c8de8fda54499bc9dd249a30133fb
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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