HCID 57219716, compound → 8-chloro-1-(chloromethyl)-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine

HRID 1413359Notes

Reaction equation

HRID 1413359 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10]([NH:12][NH:13][C:14](=O)[CH2:15][Cl:16])[CH2:9][N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:24]=1>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:14]([CH2:15][Cl:16])=[N:13][N:12]=[C:10]3[CH2:9][N:8]=[C:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]=2[CH:24]=1

Participants

3

Reactant 1

HCID 57219716HCID 57219716, compound

Product 1

HCID 126123458-chloro-1-(chloromethyl)-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of chloroacetic acid, 2-(7-chloro-5-phenyl-3H-1,4-benzodiazepin-2-yl) hydrazide (23.7 g.) in acetic acid (280 ml.), under nitrogen was placed in an oil bath that had been preheated to 140° C. After 20 minutes the mixture was cooled and concentrated in vacuo. The residue was mixed with water, neutralized with sodium bicarbonate and extracted with chloroform. The extract was washed with brine, dried over anhydrous sodium sulfate and concentrated. Crystallization of the residue from ethyl acetate gave 18.1 g. of 8-chloro-1-(chloromethyl)-6-phenyl-4H-s-triazolo[3,4-a][1,4]benzodiazepine of melting point 187°-189° C. (dec.) and 1.74 g. of melting point 187°-189° C. (dec.). This product was the same as that obtained in Preparation 2.

Workup

  1. customunder nitrogen was placed in an oil bath
  2. customhad been preheated to 140° C
  3. temperatureAfter 20 minutes the mixture was cooled
  4. concentrationconcentrated in vacuo
  5. additionThe residue was mixed with water
  6. extractionextracted with chloroform
  7. washThe extract was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customCrystallization of the residue from ethyl acetate
  11. customgave 18.1 g
  12. customthat obtained in Preparation 2

Sources & evidence

ORD record
ord-3b78b1faa4344f2bb1aa0916c0e2faa4
Source dataset
uspto-grants-1981_02
Patent number
US04250094

Reaction notes

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