Hydrochloric Acid → HCID 57279629, compound

HRID 1763371Notes

Reaction equation

HRID 1763371 reaction equation
[C:1]1([C:7]2[C:13]3[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=3[N:11]3[N:19]=[C:20]([C:22]([OH:24])=[O:23])[N:21]=[C:10]3[CH2:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:26](O)[CH3:27]>>[CH2:26]([O:23][C:22]([C:20]1[N:21]=[C:10]2[CH2:9][N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:13]3[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=3[N:11]2[N:19]=1)=[O:24])[CH3:27]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 20332965HCID 20332965, compound

Product 1

HCID 57279629HCID 57279629, compound

Procedure

6.77 g (0.020 mole) of 6-phenyl-8-chloro-4H-s-triazolo[1,5-a][1,4]benzodiazepine-2-carboxylic acid [cp. Example 1(a), (b) and (c)] is suspended in 250 ml of abs. ethanol. While being stirred and refluxed, the solution is saturated with hydrogen chloride gas. The obtained clear solution is refluxed for a further 10 hours, and afterwards concentrated at 40° in vacuo. The residue is dissolved in 100 ml of ice-cold 5% sodium bicarbonate solution and 100 ml of methylene chloride; the organic phase is separated, washed with water, dried over sodium sulphate and concentrated at 40° in vacuo. The crude greasy residue is refluxed for 1 hour with 100 ml of ether, whereby crystallisation occurs. After cooling to 0°, the crystals are filtered off under suction and washed with ether. 6-Phenyl-8-chloro-4H-s-triazolo[1,5-a] [1,4]benzodiazepine-2-carboxylic acid ethyl ester, M.P. 137°-138°, is obtained.

Workup

  1. temperaturerefluxed
  2. temperatureThe obtained clear solution is refluxed for a further 10 hours
  3. concentrationafterwards concentrated at 40° in vacuo
  4. dissolutionThe residue is dissolved in 100 ml of ice-cold 5% sodium bicarbonate solution
  5. customthe organic phase is separated
  6. washwashed with water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated at 40° in vacuo
  9. temperatureThe crude greasy residue is refluxed for 1 hour with 100 ml of ether, whereby crystallisation
  10. temperatureAfter cooling to 0°
  11. filtrationthe crystals are filtered off under suction
  12. washwashed with ether

Sources & evidence

ORD record
ord-2906d2f5d6f543f185202f2b683409c7
Source dataset
uspto-grants-1978_09
Patent number
US04111950

Reaction notes

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