Acetic Acid → 8-Nitrodibenzo[b,f]thiepin-3-carboxylic acid 5,5-dioxide

HRID 485439Notes

Reaction equation

HRID 485439 reaction equation
C(C1[CH:4]=[CH:5][C:6]2[CH:12]=[CH:11][C:10]3[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:9]=3[S:8](=[O:21])(=[O:20])[C:7]=2[CH:22]=1)#N.S(=O)(=O)(O)O.[C:28]([OH:31])(=[O:30])[CH3:29]>>[N+:17]([C:14]1[CH:15]=[CH:16][C:9]2[S:8](=[O:21])(=[O:20])[C:7]3[CH:22]=[C:29]([C:28]([OH:31])=[O:30])[CH:4]=[CH:5][C:6]=3[CH:12]=[CH:11][C:10]=2[CH:13]=1)([O-:19])=[O:18]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 202702143-Cyano-8-nitrodibenzo[b,f]thiepin-5,5-dioxide

Product 1

HCID 131518828-Nitrodibenzo[b,f]thiepin-3-carboxylic acid 5,5-dioxide

Procedure

400 Mg. 3-cyano-8-nitrodibenzo[b,f]-thiepin-5,5-dioxide is refluxed in 5 cc. acetic acid and 5 cc. 50% aqueous sulfuric acid for 24 hours. The mixture is cooled down, the crystallized material is filtered, washed with water, dried at 135° C. in vacuum to yield 345 mg. (81.2%) acid, m.p. 310°-312° C.

Workup

  1. temperatureThe mixture is cooled down
  2. filtrationthe crystallized material is filtered
  3. washwashed with water
  4. customdried at 135° C. in vacuum
  5. customto yield 345 mg

Sources & evidence

ORD record
ord-c23cc5077431430baefd76d597638745
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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