p-Toluenesulfonic acid → HCID 19010444, compound

HRID 1764533Notes

Reaction equation

HRID 1764533 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].[C:24]([O-])([O-])(OCC)[CH3:25].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH3:24][C:25]1[N:4]2[C:5]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:6]=3[C:7]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[N:8][CH2:9][C:3]2=[N:1][N:2]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 22768402HCID 22768402, compoundHCID 86598186Ethyl ortho-acetate

Product 1

HCID 19010444HCID 19010444, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 9,5 parts of 2-hydrazino-5-phenyl-7-trifluoromethyl-3-H-1,4-benzodiazepine prepared in Example 4, 29 parts of ethyl orthoacetate and 150 parts by volume of chloroform, is added dropwise 23 parts of p-toluenesulfonic acid with stirring under ice-cooling below 10° C and then the mixture is stirred at room temperature for 7 hours. After completion of the reaction, the reaction mixture is neutralized with a saturated aqueous solution of sodium bicarbonate and the chloroform layer is separated, washed with water and dried over sodium sulfate. After evaporation of the solvent, the residue is treated with a mixture of benzene and isopropyl ether, whereby 1-methyl-6-phenyl-8-trifluoromethyl-4H-s-triazolo [4,3-a] [1,4] benzodiazepine is yielded as crystals containing benzene of crystallization. Recrystallization from a mixture of benzene and n-hexane yields colorless needless melting at 129° C to 130° C (sintering), 133° C to 134° C (effervescence).

Workup

  1. temperaturecooling below 10° C
  2. stirringthe mixture is stirred at room temperature for 7 hours
  3. customAfter completion of the reaction
  4. customthe chloroform layer is separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customAfter evaporation of the solvent
  8. additionthe residue is treated with a mixture of benzene and isopropyl ether

Sources & evidence

ORD record
ord-dd3d131018d94d918951a4cc81145d83
Source dataset
uspto-grants-1978_09
Patent number
US04116956

Reaction notes

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