2H-3,1-Benzoxazine-2,4(1H)-dione, 5-nitro- → HCID 56990654, compound

HRID 223326Notes

Reaction equation

HRID 223326 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[NH:14][C:13](=[O:15])[O:12][C:10](=O)[C:9]=12)([O-:3])=[O:2].[NH:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1C(O)=O>CS(C)=O.C(O)C>[N+:1]([C:4]1[C:9]2[C:10](=[O:12])[N:16]3[CH2:23][CH2:22][CH2:21][C@H:17]3[C:13](=[O:15])[NH:14][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 1347952H-3,1-Benzoxazine-2,4(1H)-dione, 5-nitro-HCID 145742L-Proline

Product 1

HCID 56990654HCID 56990654, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

10.6 g (50.9 mmol) of 6-nitroisatoic acid anhydride and 6.1 g (50.9 mmol) of L-proline in 70 ml of dimethyl sulphoxide are heated to 90° for 45 minutes, the mixture is subsequently evaporated in a high vacuum and the residue obtained is heated to 140° for 4 hours. The crystalline crude product is taken up in 100 ml of boiling ethanol, left to stand in the cold overnight, the material obtained is filtered off under suction while back-washing with cold ethanol and dried to constant weight. There is obtained (S)-1,2,3,11a-tetrahydro-6-nitro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione which has a decomposition point of 235°-237°.

Workup

  1. customthe mixture is subsequently evaporated in a high vacuum
  2. customthe residue obtained
  3. temperatureis heated to 140° for 4 hours
  4. waitleft
  5. customto stand in the cold overnight
  6. customthe material obtained
  7. filtrationis filtered off under suction
  8. washwhile back-washing with cold ethanol
  9. customdried to constant weight

Sources & evidence

ORD record
ord-d38a46b2e90348ac94c0384742a6129d
Source dataset
uspto-grants-1982_10
Patent number
US04353827

Reaction notes

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