Ammonia → HCID 54276816, compound

HRID 1995512Notes

Reaction equation

HRID 1995512 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-db02eb2acf9c4789bdc446eef49944f7
Source dataset
uspto-grants-1983_09
Patent number
US04405516

Reaction notes

Loading…