Hydrochloric Acid → 10-methyl-5H-[1,2,4]triazolo[1,5-d][1,4]benzodiazepin-6(7H)-one

HRID 273798Notes

Reaction equation

HRID 273798 reaction equation
Cl[CH2:2][C:3]1[N:12]2[CH:13]=[N:14][N:15]=[C:11]2[C:10]2[CH:9]=[C:8]([CH3:16])[CH:7]=[CH:6][C:5]=2[N:4]=1.[OH-:17].[Na+].Cl>O1CCOCC1>[CH3:16][C:8]1[CH:7]=[CH:6][C:5]2[NH:4][C:3](=[O:17])[CH2:2][N:15]3[N:14]=[CH:13][N:12]=[C:11]3[C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 200941065-(Chloromethyl)-9-methyl-1,2,4-triazolo[4,3-c]quinazoline

Product 1

HCID 13571501610-methyl-5H-[1,2,4]triazolo[1,5-d][1,4]benzodiazepin-6(7H)-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
8 °C

Procedure

5. 62.1 g of 5-(chloromethyl)-9-methyl-1,2,4-triazolo[4,3-c]quinazoline are suspended in 1.1 l of dioxan and cooled to 8° C. 320 ml of 1N sodium hydroxide solution are added dropwise thereto within 10 min. at 7° to 10° C. The mixture is stirred at room temperature for 24 h. The reaction mixture is then made weakly acid (pH 5-6) with 2N hydrochloric acid and concentrated in a vacuum. The residue is dissolved in dichloromethane and washed with sodium chloride solution. The organic phase is dried, decolorized with Norit charcoal, filtered clear and concentrated in a vacuum to a volume of about 400 ml. After the addition of 400 ml of ethyl acetate the mixture is again concentrated to a volume of about 200 ml. The crystal slurry is left to stand at -25° C. overnight and the crystals are then filtered off. After drying in a vacuum there are obtained 35.5 g of 10-methyl-5H-[1,2,4]triazolo[1,5-d][1,4]benzodiazepin-6(7H)-one of m.p. 206°-208° C.

Workup

  1. concentrationconcentrated in a vacuum
  2. dissolutionThe residue is dissolved in dichloromethane
  3. washwashed with sodium chloride solution
  4. customThe organic phase is dried
  5. filtrationfiltered clear
  6. concentrationconcentrated in a vacuum to a volume of about 400 ml
  7. additionAfter the addition of 400 ml of ethyl acetate the mixture
  8. concentrationis again concentrated to a volume of about 200 ml
  9. waitThe crystal slurry is left
  10. waitto stand at -25° C. overnight
  11. filtrationthe crystals are then filtered off
  12. customAfter drying in a vacuum

Sources & evidence

ORD record
ord-470b9d0ae9de4e49b5349703f9d6ef71
Source dataset
uspto-grants-1995_02
Patent number
US05387585

Reaction notes

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