Hydrochloric Acid → HCID 21279101, compound

HRID 2291610Notes

Reaction equation

HRID 2291610 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:5][CH2:4][C:3]=1[CH:12]=O.[SH:14][CH:15]([CH2:19][C:20]([OH:22])=[O:21])C(O)=O.C(N(CC)CC)C.Cl>CS(C)=O.O>[S:14]1[C:2]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[S:5][CH2:4][C:3]=2[CH:12]=[C:15]1[CH2:19][C:20]([OH:22])=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6268(+-)-Mercaptosuccinic acidHCID 8471TriethylamineHCID 841814-Chloro-2H-1-benzothiopyran-3-carboxaldehyde

Product 1

HCID 21279101HCID 21279101, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 21 g 4-chloro-3-formyl-thiochrom-3-ene in 80 ml dry dimethylsulfoxide under nitrogen is added 15 g mercaptosuccinic acid. 36 ml triethylamine is then added dropwise and subsequently the reaction mixture is kept at 90°-100° C. for 30 minutes. The mixture is then diluted with water, acidified with hydrochloric acid and extracted with diethylether. The organic layer is then extracted with aqueous sodium bicarbonate solution. After acidification of the aqueous layer the product precipitates as a tar. It is taken up in chloroform. After evaporation of the solvent the residue is recrystallized from a mixture of chloroform and cyclohexane. Pure (4H-thieno[3,2-c][1]benzothiopyran-2-yl)acetic acid is obtained; m.p. 106°-110° C.

Workup

  1. extractionextracted with diethylether
  2. extractionThe organic layer is then extracted with aqueous sodium bicarbonate solution
  3. customAfter acidification of the aqueous layer the product precipitates as a tar
  4. customAfter evaporation of the solvent the residue
  5. customis recrystallized from a mixture of chloroform and cyclohexane

Sources & evidence

ORD record
ord-69775880dd92413c9aacffaa9c829d8e
Source dataset
uspto-grants-1989_01
Patent number
US04797414

Reaction notes

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