Nitric Acid → HCID 67862033, compound

HRID 5781Notes

Reaction equation

HRID 5781 reaction equation
[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([N:11]2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:13]=[C:12]2S)[CH2:3]1.[N+:21]([O-:24])([OH:23])=[O:22].[OH-].[Na+]>>[N+:21]([O-:24])([OH:23])=[O:22].[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([N:11]2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:13]=[CH:12]2)[CH2:3]1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 178418650HCID 178418650, compound

Product 1

HCID 67862033HCID 67862033, compoundYield 62.6%

Procedure

A mixture of 10 parts of methyl 1-(2,3-dihydro-3-methyl-1H-inden-1-yl)-2-mercapto-1H-imidazole-5-carboxylate and 120 parts of a nitric acid solution 30% is stirred for 30 minutes at room temperature (intense reaction). The reaction mixture is poured into crushed ice and treated with a sodium hydroxide solution. The product is extracted with trichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is converted into the nitrate salt in 2-propanone and 2,2'-oxybispropane. The salt is filtered off and dried, yielding 6.8 parts (62.6%) of methyl 1-(2,3-dihydro-3-methyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate mononitrate; mp. 140.3° C. (compound 2.35).

Workup

  1. custom(intense reaction)
  2. additionThe reaction mixture is poured
  3. custominto crushed ice
  4. extractionThe product is extracted with trichloromethane
  5. washThe extract is washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. filtrationThe salt is filtered off
  10. customdried

Sources & evidence

ORD record
ord-a725ac383d3d49d4a25d7e2303a9b53c
Source dataset
uspto-grants-1993_09
Patent number
US05246915

Reaction notes

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