Nitric Acid → HCID 70394524, compound

HRID 1762403Notes

Reaction equation

HRID 1762403 reaction equation
[CH:1]1([CH:7]([N:11]2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:13]=[C:12]2S)[CH2:8][CH2:9][CH3:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:21]([O-:24])([OH:23])=[O:22].[OH-].[Na+]>O>[N+:21]([O-:24])([OH:23])=[O:22].[CH:1]1([CH:7]([N:11]2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:13]=[CH:12]2)[CH2:8][CH2:9][CH3:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 178440811HCID 178440811, compound

Product 1

HCID 70394524HCID 70394524, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 30 parts of methyl 1-(1-cyclohexylbutyl)-2-mercapto-1H-imidazole-5-carboxylate in 150 parts of concentrated nitric acid and 100 parts of water was stirred for 1 hour at room temperature (intense reaction). The whole was cooled in crushed ice and treated with a sodium hydroxide solution. The product was extracted with 1,1'-oxybisethane. The extract was washed twice with water, dried, filtered and evaporated. The residue was converted into the nitrate salt in 2,2'-oxybispropane. The salt was filtered off and dried, yielding 27 parts (82.4%) of methyl 1-(1-cyclohexylbutyl)-1H-imidazole-5-carboxylate mononitrate; mp. 128.9° C. (compound 26).

Workup

  1. custom(intense reaction)
  2. temperatureThe whole was cooled in crushed ice
  3. extractionThe product was extracted with 1,1'-oxybisethane
  4. washThe extract was washed twice with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. filtrationThe salt was filtered off
  9. customdried

Sources & evidence

ORD record
ord-6b76eb986adb477d9473509d3a35bb26
Source dataset
uspto-grants-1989_05
Patent number
US04832732

Reaction notes

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