Nitric Acid → methyl 1-(decahydro-1-napthalenyl)-1H-imidazole-5-carboxylate mononitrate

HRID 621389Notes

Reaction equation

HRID 621389 reaction equation
[CH:1]1([N:11]2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:13]=[C:12]2S)[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.[N+:21]([O-:24])([OH:23])=[O:22].N([O-])=O.[Na+].[OH-].[Na+]>O>[N+:21]([O-:24])([OH:23])=[O:22].[CH:1]1([N:11]2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:13]=[CH:12]2)[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 178498868HCID 178498868, compound

Product 1

HCID 21242533methyl 1-(decahydro-1-napthalenyl)-1H-imidazole-5-carboxylate mononitrateYield 39.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 77.7 parts of methyl 1-(decahydro-1-naphthalenyl)-2-mercapto-1H-imidazole-5-carboxylate, 157 parts of nitric acid, 300 parts of water and 0.2 parts of sodium nitrite was stirred for 1.5 hours at room temperature. The reaction mixture was poured into crushed ice and treated with a sodium hydroxide solution. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was converted into the nitrate salt in 1,1'-oxybisethane. The salt was filtered off and dried, yielding 33.9 parts (39.4%) of methyl 1-(decahydro-1-napthalenyl)-1H-imidazole-5-carboxylate mononitrate; mp. 148.6° C. (compound 1.03).

Workup

  1. additionThe reaction mixture was poured
  2. custominto crushed ice
  3. extractionThe product was extracted with dichloromethane
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. filtrationThe salt was filtered off
  8. customdried

Sources & evidence

ORD record
ord-85ad0d5d51844f09a12264b86c3da327
Source dataset
uspto-grants-1989_04
Patent number
US04824472

Reaction notes

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