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

HRID 485098Notes

Reaction equation

HRID 485098 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.C(O)=[O:21]>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:21])[CH:4]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 13151874HCID 13151874, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Mix 267 mg (1 mmole) 3-cyano-dibenzo[b,f]thiepin-5,5-dioxide with Raney allowy (500 mg) and a mixture of 4 ml formic acid and 1 ml water at the reflux temperature. After 3 hours, add 200 mg additional Raney alloy and heat for one hour to obtain complete reduction. Filter the reaction mixture while hot to remove the alloy, and wash with ethyl acetate to remove any occluded solvent. Wash the organic layer containing the product with water and with saturated sodium chloride solution. Separate the organic layer containing the product to produce a residue of a pale yellow oil, which crystallizes in a small volume of ethyl acetate, m.p. 167°-171° C.

Workup

  1. additionadd 200 mg additional Raney alloy
  2. temperatureheat for one hour
  3. customto obtain complete reduction
  4. filtrationFilter the reaction mixture while hot
  5. customto remove the alloy
  6. washwash with ethyl acetate
  7. customto remove any occluded solvent
  8. washWash the organic layer
  9. additioncontaining the product with water
  10. customSeparate the organic layer
  11. additioncontaining the product
  12. customto produce a residue of a pale yellow oil, which
  13. customcrystallizes in a small volume of ethyl acetate, m.p. 167°-171° C.

Sources & evidence

ORD record
ord-99459c61b20a47afaca1e37efafff414
Source dataset
uspto-grants-1985_08
Patent number
US04535171

Reaction notes

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