Acetic Acid → 8-Chlorodibenzo[b,f]thiepin-3-carboxylic acid

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=C(C#N)[CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:18]=1.S(=O)(=O)(O)O.[C:24]([OH:27])(=[O:26])[CH3:25]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[C:25]([C:24]([OH:27])=[O:26])[CH:14]=[CH:15][C:9]=3[CH:8]=[CH:7][C:6]=2[CH:18]=1

Participants

Reactant 3

HCID 176Acetic Acid

HCID 1118Sulfuric Acid

HCID 131518898-Chloro-3-cyanodibenzo[b,f]thiepin

Product 1

HCID 131518918-Chlorodibenzo[b,f]thiepin-3-carboxylic acid

Procedure

550 Mg. 8-chloro-3-cyanodibenzo[b,f]thiepin is refluxed for 16 hours in a mixture of 15 cc. acetic acid and 15 cc. 50% aqueous sulfuric acid. The reaction mixture is cooled down and the product filtered, washed with water, and dried to yield 485 mg. (82% of the pure acid, m.p. 302°-304° C.