Itaconic acid → 3-(Benzothiazol-2-ylthio)-propane-1,2-dicarboxylic acid

HRID 65123

Reaction equation

HRID 65123 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[SH:5][C:6]1[S:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1.[C:15]([OH:23])(=[O:22])[C:16]([CH2:18][C:19]([OH:21])=[O:20])=[CH2:17].O>C(OCC)C.C(OCC)(=O)C>[S:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=[C:6]1[S:5][CH2:17][CH:16]([C:15]([OH:23])=[O:22])[CH2:18][C:19]([OH:21])=[O:20]

Participants

7

Reactant 4

HCID 811Itaconic acidHCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 178418395HCID 178418395, compound

Product 1

HCID 194275373-(Benzothiazol-2-ylthio)-propane-1,2-dicarboxylic acidYield 50.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

13.3 g of AlCl3 are dissolved in 100 ml of diethyl ether at 0° to 5°. 3.4 g of 2-mercaptobenzothiazole and 2.6 g of itaconic acid are then added. After the mixture has been stirred at 20°-25° for 24 hours, the ether solution is poured off and the residue is stirred with 100 ml of water and 100 ml of ethyl acetate. The organic phase is separated off, dried and evaporated. 3 g of 3-(benzothiazol-2-ylthio)-propane-1,2-dicarboxylic acid are obtained as the residue.

Workup

  1. customThe organic phase is separated off
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-7b1fd30bd3da47a381b20f84f472db06
Source dataset
uspto-grants-1986_09
Patent number
US04612378

Linked notes

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