Ammonia → HCID 57236670, compound

HRID 2399149Notes

Reaction equation

HRID 2399149 reaction equation
[I-].[K+].[CH2:3]([N:5]([CH2:30][CH3:31])[C:6]([C:8]1[N:12]=[C:11]([CH2:13]Cl)[N:10]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[C:22](=O)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:9]=1)=[O:7])[CH3:4].[NH3:32]>O.O1CCOCC1>[CH2:30]([N:5]([CH2:3][CH3:4])[C:6]([C:8]1[N:12]=[C:11]2[CH2:13][N:32]=[C:22]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:16]3[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=3[N:10]2[N:9]=1)=[O:7])[CH3:31]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 4875Potassium IodideHCID 20309841HCID 20309841, compound

Product 1

HCID 57236670HCID 57236670, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

An amount of 1.99 g (0.012 mole) of potassium iodide is dissolved in 6 ml of water. The obtained solution is diluted with 20 ml of dioxane; an addition is then made at 25°, with stirring, of a solution of 4.3 g (0.01 mole) of N,N-diethyl-1-(2-benzoyl-4-chlorophenyl)-5-(chloromethyl)-1H-1,2,4-triazole-3-carboxamide in 40 ml of dioxane, and the reaction solution heated for one hour at 50°. There is then added 35 ml of conc. aqueous ammonia solution, the mixture heated for a further 2 hours at 50°, and subsequently concentrated in vacuo. Water is added to the residue and extraction performed twice with methylene chloride. The organic phase is washed with water and saturated sodium chloride solution; it is then dried over sodium sulphate and concentrated in vacuo to dryness. The residue is recrystallized from benzene/cyclohexane to obtain pure N,N-diethyl-6-phenyl-8-chloro-4H-s-triazolo[1,5-a][1,4]benzodiazepine-2-carboxamide, M.P. 175°-177°.

Workup

  1. additionan addition
  2. customis then made at 25°
  3. temperaturethe reaction solution heated for one hour at 50°
  4. temperaturethe mixture heated for a further 2 hours at 50°
  5. concentrationsubsequently concentrated in vacuo
  6. additionWater is added to the residue and extraction
  7. washThe organic phase is washed with water and saturated sodium chloride solution
  8. dry with materialit is then dried over sodium sulphate
  9. concentrationconcentrated in vacuo to dryness
  10. customThe residue is recrystallized from benzene/cyclohexane

Sources & evidence

ORD record
ord-6b5e4d8e3b194bb8ada219656ffcbc3a
Source dataset
uspto-grants-1977_05
Patent number
US04027029

Reaction notes

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