Nitric Acid → HCID 14305178, compound

HRID 622310Notes

Reaction equation

HRID 622310 reaction equation
S[C:2]1[N:3]([CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=1.N([O-])=O.[Na+].[N+]([O-])(O)=O.[OH-].[Na+]>O>[C:18]1([CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:3]2[C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:6]=[CH:2]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 178498870HCID 178498870, compound

Product 1

HCID 14305178HCID 14305178, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 123.6 parts of methyl 2-mercapto-1-[phenyl(2-pyridinyl)methyl]-1H-imidazole-5-carboxylate, 0.2 parts of sodium nitrite, 219 parts of nitric acid and 440 parts of water was stirred for 2 hours at room temperature. The reaction mixture was poured into water and the whole was treated with a sodium hydroxide solution (on an ice bath). The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized twice: first from 2-propanone and then from 4-methyl-2-pentanone. The product was filtered off (the filtrates were set aside) and dried in vacuo at 70° C., yielding a first fraction of 37.2 parts (33.3%) of methyl 1-[phenyl(2-pyridinyl)methyl]-1H-imidazole-5-carboxylate; mp. 96.3° C.

Workup

  1. extractionThe product was extracted with dichloromethane
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was crystallized twice
  6. filtrationThe product was filtered off (the filtrates
  7. customdried in vacuo at 70° C.

Sources & evidence

ORD record
ord-37e9f4913b44469bb8ace423cf802f27
Source dataset
uspto-grants-1988_09
Patent number
US04770689

Reaction notes

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