Utilization of phosphorus pentasulfide in thionylations...

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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Reexamination Certificate

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06960669

ABSTRACT:
A method is disclosed for the preparation of benzo[b]thiophenecarbodithioic esters of the formula:wherein R is alkyl, R1is hydrogen, halogen, or alkyl, R2, R3, R4, and R5are independently selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, alkylthio, trifluoromethyl, cyano, and aryl,wherein said method comprises reacting an equivalent of an S-thiol ester of the formula:with one-third of an equivalent of P2S5, 2 equivalents of at least one alkali metal carbonate, about 2.5 mole percent of a phase transfer catalyst, and a catalytic amount of water in hot toluene.

REFERENCES:
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patent: 5965749 (1999-10-01), Brouwer
patent: 6372297 (2002-04-01), Davis et al.
patent: 6555697 (2003-04-01), Schlama
patent: 0715625 (1997-06-01), None
patent: 95/06043 (1995-03-01), None
Sudalai et al., A Mild and Versatile Catalyst/Reagent for the Preparation of Dithiocarboxylic Esters, Organic Letters, vol. 2, No. 20, pp. 3213-3216, (2000).
Davy et al., One Pot Synthesis of Dithio-esters from Carboxylic Acids, Alcohols, and PS, Chemistry and Industry, p. 824, Dec. 1985.
Rao et al., A PTC Assisted Thionation: Synthesis of 2H-1,4-Benzoxazine-3(4H)-Thiones & 2H-1,4-Benzothiazine-3(4H)-Thiones, Synthetic Communications, 31(22), pp. 3469-3472 (2001).

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