Synthesis of 3- (Carboxymethyl) Benzothiazoline-2-Thione

Attempts to thermally rearrange 2‐benzothiazolylthioacetonitrile (1) to the titled compound 8 failed. The reaction of 3‐chloromethyl‐2‐benzothiazolinethione with potassium cyanide in dimethylformamide (DMF) or dimethylsulfoxide (DMSO) at 25‐30° afforded 8 in 98% yield. Whereas replacing the DMF or DMSO solvent with acetone furnished the unexpected sulfide 9 in 92% yield. Substituting 3‐chloromethyl‐2‐benzoxazoline‐thione as the electrophile in the same reaction gave the sulfide 10 in 95% yield. Possible mechanisms and supporting nmr data are discussed.

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Synthesis of 2‐oxo and 2‐thioxo‐3(2H)‐benzothiazoleethanimic acid anhydride with acetic acid and related products

D'Amico

Bellinger

Freeman

1988

Journal of Heterocyclic Chem

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The reaction of the appropriate 2‐benzothiazolinone with 2‐chloroacetamide under basic conditions afforded the 2‐oxo‐3(2H)‐benzothiazolineacetamides 6–9. The 2‐thioxo‐3(2H)‐benzothiazolineacetamide (10) was prepared by the reaction of 3‐(carbethoxymethyl)benzothiazoline‐2‐thione with ammonium hydroxide. The reaction of acetamides 6–10 with the appropriate anhydride containing a catalytic amount of the sodium salt of the acid corresponding to the anhydride afforded the titled compounds 11–18 in excellent yields. The omission of the catalyst in the same reaction furnished a mixture containing 57% of the titled compound, 37% of the nitrile and 6% of an unknown. Possible mechanism and supporting nmr, ir and mass spectral data are discussed.

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Synthesis of 3- (Carboxymethyl) Benzothiazoline-2-Thione

Cited by 5 publications

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ChemInform Abstract: SYNTHESIS OF 3‐(CARBOXYMETHYL)BENZOTHIAZOLINE‐2‐THIONE

ChemInform Abstract: SYNTHESIS OF 3‐(CARBOXYMETHYL)BENZOTHIAZOLINE‐2‐THIONE

Synthesis of 2‐thioxo‐3‐benzothiazolineacetonitrile and related products

Synthesis of 2‐oxo and 2‐thioxo‐3(2H)‐benzothiazoleethanimic acid anhydride with acetic acid and related products

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