Nitric Acid → HCID 20271490, compound

HRID 485105Notes

Reaction equation

HRID 485105 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]2[S:12][C:11]3[CH:13]=[C:14]([CH:17]=[O:18])[CH:15]=[CH:16][C:10]=3[CH:9]=[CH:8][C:7]=2[CH:19]=1.[N+]([O-])(O)=[O:21].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]2[S:12](=[O:21])[C:11]3[CH:13]=[C:14]([CH:17]=[O:18])[CH:15]=[CH:16][C:10]=3[CH:9]=[CH:8][C:7]=2[CH:19]=1

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 516892Sodium BicarbonateHCID 20271502HCID 20271502, compound

Product 1

HCID 20271490HCID 20271490, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 8-methylthiodibenzo[b,f]thiepin-3-carboxaldehyde (5 mmole) in methylene chloride (100 ml); and while cooling the solution in an ice-bath, add a 1M solution of 90% nitric acid in methylene chloride (5 ml). Monitor the reaction mixture by tlc after 30 minutes, and add the nitric acid solution in small increments until starting material has disappeared. Treat the reaction mixture with sodium bicarbonate solution to remove acidic substances. Dry the organic solution, evaporate to dryness, and purify the title product by column chromatography on silica gel using 1:4 ethyl acetate/toluene for elution.

Workup

  1. temperatureand while cooling the solution in an ice-bath
  2. customto remove acidic substances
  3. customDry the organic solution
  4. customevaporate to dryness
  5. custompurify the title product by column chromatography on silica gel using 1:4 ethyl acetate/toluene
  6. washfor elution

Sources & evidence

ORD record
ord-3ee581d9baf84b46aeee10496c6f07ed
Source dataset
uspto-grants-1985_08
Patent number
US04535171

Reaction notes

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