Toluene → HCID 12617933, compound

HRID 1701286Notes

Reaction equation

HRID 1701286 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[NH:7][C:6](=O)[C:5]=12.P(Cl)(Cl)(Cl)(Cl)Cl.[C:22]1([CH3:28])C=CC=CC=1>CN(C)C=O>[CH3:3][N:4]1[CH2:28][CH2:22][N:7]([C:6]2[C:5]3=[CH:1][CH:2]=[CH:3][N:4]3[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24819Phosphorus pentachlorideHCID 4682545,10-Dihydro-11H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one

Product 1

HCID 12617933HCID 12617933, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 2 g. of 5,10-dihydro-11H-pyrrolo[2,1-c]-[1,4]benzodiazepin-11-one (Example 1), 2 g. of phosphorus pentachloride and two drops of N,N-dimethylformamide in 50 ml. of toluene is heated on the steam bath for several hours. The solvent is removed by distillation, 25 ml. of chloroform is added and the mixture evaporated again. The residue is dissolved in 25 ml. of chloroform and this solution slowly added to 10 ml. of N-methylpiperazine in 40 ml. of toluene. This mixture is heated for several hours, finally to the boiling point of toluene, and then evaporated to an oily residue. The residue is taken up in ether (500 ml) and extracted into dilute acetic acid. The aqueous acetic acid layer is made basic with concentrated ammonium hydroxide and the product which precipitates is extracted into ether. The ether solution is dried over anhydrous potassium carbonate, and evaporated to a residue which contains the desired product. When purified by recrystallization it shows m.p. 139°-141° C. (base).

Workup

  1. additionA mixture of 2 g
  2. customThe solvent is removed by distillation, 25 ml
  3. additionof chloroform is added
  4. customthe mixture evaporated again
  5. dissolutionThe residue is dissolved in 25 ml
  6. additionof chloroform and this solution slowly added to 10 ml
  7. temperatureThis mixture is heated for several hours, finally to the boiling point of toluene
  8. customevaporated to an oily residue
  9. extractionextracted into dilute acetic acid
  10. customthe product which precipitates
  11. extractionis extracted into ether
  12. dry with materialThe ether solution is dried over anhydrous potassium carbonate
  13. customevaporated to a residue which
  14. customWhen purified by recrystallization it

Sources & evidence

ORD record
ord-fe773524fbae4007b392c33fb754ce47
Source dataset
uspto-grants-1980_03
Patent number
US04192803

Reaction notes

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