2-Chlorobenzothiazole → Methyl α-(2-benzothiazolylthio)benzeneacetate

HRID 848109Notes

Reaction equation

HRID 848109 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH:4]([SH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[H-].[Na+].Cl[C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.BrC1SC2C=CC=CC=2N=1>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[CH:4]([S:11][C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 119872-ChlorobenzothiazoleHCID 24758Sodium hydrideHCID 6120402-Bromo-1,3-benzothiazoleHCID 12900987HCID 12900987, compound

Product 1

HCID 54106029Methyl α-(2-benzothiazolylthio)benzeneacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

18.2 g of 2-mercapto-2-phenylacetic acid methyl ester is added to a suspension of 2.4 g of NaH in 200 ml of DMF and the mixture is stirred until the evolution of gas has ceased. 17 g of 2-chlorobenzothiazole (or 21.5 g of 2-bromobenzothiazole) is then introduced. The mixture is stirred for 5 hours at 80° and is worked up in the customary manner to give 2-(benzothiazol-2-ylthio)-2-phenylacetic acid methyl ester, in the form of an oil.

Workup

  1. stirringThe mixture is stirred for 5 hours at 80°

Sources & evidence

ORD record
ord-75d9164de36b4c3fa3658f3996a3c7f7
Source dataset
uspto-grants-1981_10
Patent number
US04294839

Reaction notes

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