p-Toluenesulfonic acid → HCID 86736040, compound

HRID 1764532Notes

Reaction equation

HRID 1764532 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]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:19][C:5]=2[N:4]=1)[NH2:2].[CH:24]([O-])([O-])OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[C:10]1([C:7]2[C:6]3[CH:16]=[C:17]([C:20]([F:23])([F:22])[F:21])[CH:18]=[CH:19][C:5]=3[N:4]3[CH:24]=[N:2][N:1]=[C:3]3[CH2:9][N:8]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 22768402HCID 22768402, compoundHCID 53630039Ethylorthoformate

Product 1

HCID 86736040HCID 86736040, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 3.2 parts of 2-hydrazino-5-phenyl-7-trifluoromethyl-3H-1,4-benzodiazepine, prepared in Example 4, 8.5 parts of ethyl orthoformate and 50 parts by volume of chloroform, is added dropwise 7.6 parts of p-toluenesulfonic acid at a temperature below 10° C. The mixture is stirred at room temperature for 2.5 hours. After completion of the reaction, the reaction mixture is neutralized with a saturated aqueous solution of sodium bicarbonate. The chloroform layer is separated, washed with water and dried over sodium sulfate. Evaporation of the solvent yields 6-phenyl-8-trifluoromethyl-4H-s-triazolo [4,3-a] [1,4] benzodiazepine as crystals. The crystals are dissolved in ethanol and the insoluble material is removed by filtration. The filtrate is concentrated and recrystallized from ethyl acetate to give colorless flakes. Melting point: 258° C to 260° C.

Workup

  1. customAfter completion of the reaction
  2. customThe chloroform layer is separated
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-93d961e7424f42a8b632672e9febe3bd
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

Loading…