Nitric Acid → HCID 18537632, compound

HRID 412385Notes

Reaction equation

HRID 412385 reaction equation
[Cl:1][CH2:2][C:3]1[N:20]([CH3:21])[C:6]2=[N:7][C:8]([S:11][C:12]3[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=3)=[CH:9][CH:10]=[C:5]2[N:4]=1.S(=O)(=O)(O)O.[N+:27]([O-])([OH:29])=[O:28]>C(O)(=O)C>[Cl:1][CH2:2][C:3]1[N:20]([CH3:21])[C:6]2=[N:7][C:8]([S:11][C:12]3[CH:13]=[C:14]([CH3:19])[C:15]([N+:27]([O-:29])=[O:28])=[C:16]([CH3:18])[CH:17]=3)=[CH:9][CH:10]=[C:5]2[N:4]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 18537661HCID 18537661, compound

Product 1

HCID 18537632HCID 18537632, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 2-chloromethyl-5-(3,5-dimethylphenylthio)-3-methyl-3H-imidazo[4,5-b]pyridine (2.54 g), sulfuric acid (5 ml) and acetic acid (45 ml) was added nitric acid (0.52 ml) in an ice bath. The mixture was allowed to stand at room temperature for 64 hours. The reaction mixture was concentrated, diluted with water, neutralized with sodium bicarbonate and then extracted with ethyl acetate. The extract was concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=1:1 as the eluant to afford the desired compound (0.53 g, mp 133-135° C.).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. concentrationThe extract was concentrated
  5. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-af5eebc8f4aa4132b26be0d086299222
Source dataset
uspto-grants-2003_05
Patent number
US06562849B1

Reaction notes

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