Ammonia → HCID 12317882, compound

HRID 437771Notes

Reaction equation

HRID 437771 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-])=[O:20])[CH:17]=[CH:18][C:13]=2[N:12]2[C:22]([CH3:25])=[N:23][N:24]=[C:11]2[CH2:10][N:9]=1.O1CCCC1.O.O.O.C([O-])(=O)C.[Na+].N>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([NH:19][OH:20])[CH:17]=[CH:18][C:13]=2[N:12]2[C:22]([CH3:25])=[N:23][N:24]=[C:11]2[CH2:10][N:9]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 12317881ClonazolamHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 12317882HCID 12317882, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.55 g (0.01 m) of 6-(2-chlorophenyl)-1-methyl-8-nitro-4H-s-triazolo[4,3-a][1,4]benzodiazepine, 200 ml of tetrahydrofuran, 100 ml of methanol, 13.6 g of sodium acetate trihydrate and 12 g of stannous chloride dihydrate was stirred at room temperature for 1 hr under nitrogen atmosphere. After addition of 5 ml of conc. aqueous ammonia the inorganic material was separated by filtration over celite. The filter cake was washed with 500 ml of methylene chloride containing 20% of ethanol. The filtrate was evaporated and the residue was stirred with 100 ml of water and 30 ml of methylene chloride. The crystalline material was collected and washed successively with water, ethanol and ether to yield the above-named product. For analysis it was recrystallized from tetrahydrofuran/methanol, mp. 276°-278° dec.

Workup

  1. customwas separated by filtration over celite
  2. washThe filter cake was washed with 500 ml of methylene chloride containing 20% of ethanol
  3. customThe filtrate was evaporated
  4. stirringthe residue was stirred with 100 ml of water and 30 ml of methylene chloride
  5. customThe crystalline material was collected
  6. washwashed successively with water, ethanol and ether
  7. customto yield the above-named product
  8. customFor analysis it was recrystallized from tetrahydrofuran/methanol, mp. 276°-278° dec.

Sources & evidence

ORD record
ord-ed84a3332c1548958d66d15eff45500c
Source dataset
uspto-grants-1977_06
Patent number
US04032535

Reaction notes

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