Dimethyl itaconate → HCID 20212281, compound

HRID 1906539Notes

Reaction equation

HRID 1906539 reaction equation
[SH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11]([O:20][CH3:21])(=[O:19])[C:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH2:13]>S(=O)(=O)(O)O>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[S:1][CH2:13][CH:12]([C:11]([O:20][CH3:21])=[O:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 69240Dimethyl itaconateHCID 178418395HCID 178418395, compound

Product 1

HCID 20212281HCID 20212281, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

16.8 g of finely powdered 2-mercaptobenzothiazole are suspended in 150 ml of 70% sulfuric acid and 16.6 g of dimethyl itaconate are added dropwise at 0°-10° in the course of half an hour, with stirring. After further 16 hours at 0°-10°, the reaction mixture is poured into ice water and extracted with ethyl acetate. The organic phase is separated, dried and the solvent is evapourated. The solid residue is recristallied from cyclohexane yielding dimethyl 3-(benzothiazol-2-ylthio)-propane-1,2-dicarboxylate, melting at 46°-47°.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is separated
  3. customdried

Sources & evidence

ORD record
ord-49c5b5b100d04c1daab05888c0d6c399
Source dataset
uspto-grants-1987_03
Patent number
US04652653

Reaction notes

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