Ammonia → Ethyl 5-methyl-8-nitro-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate

HRID 851643Notes

Reaction equation

HRID 851643 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:4]2[CH2:3]1.N.[N+:23]([O-])([OH:25])=[O:24]>S(=O)(=O)(O)O>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[C:11]([N+:23]([O-:25])=[O:24])[CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 944Nitric AcidHCID 127597Ro 14-7437

Product 1

HCID 15480886Ethyl 5-methyl-8-nitro-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2.85 g of ethyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate are dissolved in a mixture of 10 ml of 98 percent nitric acid and 15 ml of 98 percent sulphuric acid and heated to 120° for 2 hours. Subsequently, the mixture obtained is cooled to room temperature, poured onto ice, neutralized with about 25 percent ammonia and extracted with chloroform. The chloroform extracts are dried over magnesium sulphate and evaporated. After recrystallization of the residue from ethyl acetate, there is obtained ethyl 5,6-dihydro-5-methyl-8-nitro-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 197°-198°.

Workup

  1. temperatureheated to 120° for 2 hours
  2. customSubsequently, the mixture obtained
  3. additionpoured onto ice
  4. extractionextracted with chloroform
  5. dry with materialThe chloroform extracts are dried over magnesium sulphate
  6. customevaporated
  7. customAfter recrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-d42eda0dde9647e195497ce89b5f6645
Source dataset
uspto-grants-1983_05
Patent number
US04386028

Reaction notes

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