Acetic Acid → Dibenzo[b,f]thiepin-3-carboxaldehyde 5,5-dioxide

HRID 485099Notes

Reaction equation

HRID 485099 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[S:8](=[O:18])(=[O:17])[C:7]=2[CH:19]=1)#N.N1C=CC=CC=1.C(O)(=[O:28])C.[PH2]([O-])=O.[Na+]>[Ni].O>[CH:5]1[C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=3[S:8](=[O:18])(=[O:17])[C:7]=2[CH:19]=[C:3]([CH:1]=[O:28])[CH:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 13151874HCID 13151874, compoundHCID 178527019HCID 178527019, compound

Product 1

HCID 13520245Dibenzo[b,f]thiepin-3-carboxaldehyde 5,5-dioxide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Mix 267 mg (1 mmole) of 3-cyano-dibenzo[b,f]thiepin-5,5-dioxide, 10 ml pyridine, 5 ml acetic acid, and 5 ml water. Add 0.5 g sodium hypophosphite and approximately 0.1 g Raney nickel. Stir at 25° C. for 24 hours and then at 45°-50° C. for 2 hours. Filter the reaction mixture to remove the catalyst and wash any product from the catalyst using 10 ml ethyl acetate. Add 10 ml 6N hydrochloric acid and separate the organic layer containing the product. Evaporate the organic layer to obtain a solid residue comprising the title product, m.p., 175°-177° C. Swishing with methanol and drying the residue gives product melting at 177°-178° C.

Workup

  1. waitat 45°-50° C. for 2 hours
  2. filtrationFilter the reaction mixture
  3. customto remove the catalyst
  4. washwash any product from the catalyst
  5. additionAdd 10 ml 6N hydrochloric acid
  6. customseparate the organic layer
  7. additioncontaining the product
  8. customEvaporate the organic layer
  9. customto obtain a solid residue

Sources & evidence

ORD record
ord-f25086cc72244b918ad76c1626d96615
Source dataset
uspto-grants-1985_08
Patent number
US04535171

Reaction notes

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