Nitric Acid → HCID 23050709, compound

HRID 1762046Notes

Reaction equation

HRID 1762046 reaction equation
S[C:2]1[N:3]([CH:11]2[CH2:24][CH:23]3[CH:18]([CH2:19][CH2:20][CH2:21][CH2:22]3)[C:17]3[C:12]2=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=1.[N+]([O-])(O)=O.[OH-].[Na+]>O>[CH2:22]1[CH:23]2[CH:18]([C:17]3[C:12]([CH:11]([N:3]4[C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=[CH:2]4)[CH2:24]2)=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:19][CH2:20][CH2:21]1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 178498867HCID 178498867, compound

Product 1

HCID 23050709HCID 23050709, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 19.0 parts of methyl 2-mercapto-1-(1,2,3,4,4a,9,10,10a-octahydro-9-phenanthrenyl)-1H-imidazole-5-carboxylate, 75 parts of nitric acid and 150 parts of water was stirred for 1 hour at room temperature. The reaction mixture was diluted with crushed ice and treated with a sodium hydroxide solution. The product was extracted with 1,1'-oxybisethane. The extract was dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 1.9 parts (11.1%) of methyl 1-(1,2,3,4,4a,9,10,10a-octahydro-9-phenanthrenyl)-1H-imidazole-5-carboxylate; mp. 139.9° C. (compound 3.2).

Workup

  1. additionThe reaction mixture was diluted with crushed ice
  2. extractionThe product was extracted with 1,1'-oxybisethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from acetonitrile
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-e3c9c298e64f439c99f11f3ca9587fca
Source dataset
uspto-grants-1989_05
Patent number
US04830664

Reaction notes

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