Sulfuric Acid → HCID 69998297, compound

HRID 1634042Notes

Reaction equation

HRID 1634042 reaction equation
OS(O)(=O)=O.[N+:6]([O-:9])([O-])=[O:7].[K+].[CH2:11]([O:13][C:14](=[O:30])[CH2:15][N:16]1[C:22](=[O:23])[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[N:19]([CH3:28])[C:18](=[O:29])[CH2:17]1)[CH3:12]>ClCCl>[CH2:11]([O:13][C:14](=[O:30])[CH2:15][N:16]1[C:22](=[O:23])[C:21]2[CH:24]=[C:25]([N+:6]([O-:9])=[O:7])[CH:26]=[CH:27][C:20]=2[N:19]([CH3:28])[C:18](=[O:29])[CH2:17]1)[CH3:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 70001132HCID 70001132, compound

Product 1

HCID 69998297HCID 69998297, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To conc H2SO4 (14 ml), kept in an ice bath, KNO3 (2 g, 20 mmol) was added in portions whereby the temperature rose to 10° C. (see also R. I. Fryer et al., J. Heterocyclic Chem. 1991, 28, 1203-1208). To this mixture was added a solution of (1-methyl-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-acetic acid ethyl ester (5 g, 18 mmol) in dichloromethane (16 ml) whereby the temperature was kept between 20-25° C. After stirring for 90 min the mixture was carefully poured onto ice water and extracted with dichloromethane. The organic extracts were washed with aqueous sat. NaHCO3 followed by water, dried over Na2SO4 and the solvents evaporated. Upon addition of EtOH to the oily residue a precipitate was formed which was collected by filtration to give (1-methyl-7-nitro-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-acetic acid ethyl ester (4 g): mp. 129-130° C.; MS (EI): 321 (M)+.

Workup

  1. customrose to 10° C.
  2. customwas kept between 20-25° C
  3. additionwas carefully poured onto ice water
  4. extractionextracted with dichloromethane
  5. washThe organic extracts were washed with aqueous sat. NaHCO3
  6. dry with materialdried over Na2SO4
  7. customthe solvents evaporated
  8. additionUpon addition of EtOH to the oily residue a precipitate
  9. customwas formed which
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-c53483a1b2964b5b986aa05eca02ff94
Source dataset
uspto-grants-2003_01
Patent number
US06506744B1

Reaction notes

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