Ammonia → HCID 54276816, compound

HRID 223184Notes

Reaction equation

HRID 223184 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:5]2[C@@H:4]2[CH2:21][CH2:22][CH2:23][N:3]12.N.[N+:25]([O-])([OH:27])=[O:26]>S(=O)(=O)(O)O>[N+:25]([C:10]1[CH:11]=[CH:12][C:7]2[N:6]3[CH:13]=[N:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:5]3[C@@H:4]3[CH2:21][CH2:22][CH2:23][N:3]3[C:2](=[O:1])[C:8]=2[CH:9]=1)([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 944Nitric AcidHCID 10041121Ethyl (7S)-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate

Product 1

HCID 54276816HCID 54276816, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3.11 g of ethyl (S)-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate in a mixture of 10 ml of 98 percent nitric acid and 15 ml of 98 percent sulphuric acid is heated to 100° for 6 hours. Subsequently, the mixture 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. The residue is recrystallized from ethyl acetate and yields ethyl (S)-11,12,13,13a-tetrahydro-7-nitro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxylate of melting point 193°-194°.

Workup

  1. temperatureis heated to 100° for 6 hours
  2. additionpoured onto ice
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform extracts are dried over magnesium sulphate
  5. customevaporated
  6. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-97ae846ae0d84e33b0124a8659aaf27b
Source dataset
uspto-grants-1982_10
Patent number
US04352815

Reaction notes

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