Water → HCID 22592708, compound

HRID 465286Notes

Reaction equation

HRID 465286 reaction equation
[CH2:1]=[C:2]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[C:3]([OH:5])=[O:4].[SH:11][C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1.O>OS(O)(=O)=O>[S:13]1[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=[C:12]1[S:11][CH2:1][CH:2]([C:3]([OH:5])=[O:4])[CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 962Water2×HCID 951552-Methyleneglutaric acidHCID 178418395HCID 178418395, compound

Product 1

HCID 22592708HCID 22592708, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

20.9 g of 2-methyleneglutaric acid are dissolved at 50°, with stirring, in 150 ml of 75% H2SO4, and 24.2 g of 2-mercaptobenzthiazole are added slowly. The reaction is exothermic and the temperature rises to 60°. The reaction mixture is then stirred for 2 hours at 55°. The resulting brown solution is poured into 500 ml of water and stirred for 1 hour. 600 ml of water are then added, and the white precipitate is filtered off. Recrystallisation from aqueous methanol gives 4-(benzthiazol-2-ylthio)-butane-1,3-dicarboxylic acid, melting at 152°-154°.

Workup

  1. customrises to 60°
  2. stirringstirred for 1 hour
  3. filtrationthe white precipitate is filtered off
  4. customRecrystallisation from aqueous methanol

Sources & evidence

ORD record
ord-66f733d14c8c4a8aa1be8ff73734207e
Source dataset
uspto-grants-1992_10
Patent number
US05152929

Reaction notes

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