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22nd August 2013 @ 14:14

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Reaction information

*#Reaction file
reactionscheme_1 .cdx
*Reaction file type CDX
*Procedure To a stirred solution of 4-iodophenol (7.70 g, 35.0 mmol) in DMF (35 mL), in a 100 mL rbf, was added NaH (1.40 g of a 60% dispersion in mineral oil, 35.0 mmol, 1.00 eq.) in small portions, at r.t. After 10 minutes the reaction vessel was heated to 80 ºC over a period of 45 minutes, and then allowed to cool to r.t. before adding dimethylthiocarbamoyl chloride (5.20 g, 42.1 mmol, 1.20 eq.) in small portions. The reaction mixture was stirred for 20 h at r.t., monitoring the disappearance of starting materials by TLC. Once most of the DMF had been removed with a rotary evaporator, the mixture was poured into DCM and washed with water; the water was extracted with DCM, and the combined organic phases were dried over anhydrous MgSO4; evaporation of the solvent afforded the crude title compound (11.42 g). The pure product, a white solid (6.93 g, 22.6 mmol, yield 64%), was obtained by column chromatography on silica gel, using as eluent (8/1) hexane/DCM (Rf 0.5).
*Yield (%) 64 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p11.pdf
PhD Thesis - 16Sep2010_final p105.pdf
Further information O-4-Iodophenyl-N,N-dimethylthiocarbamate

For multistep reactions (or their steps):

Overall reaction? False
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step Reaction 2: Rearrangement from O-carbamate to S-carbamate: S-4-Iodothiophenyl-N,N-dimethylcarbamate
Attached Files
PhD Thesis - 16Sep2010_final p11.pdf
PhD Thesis - 16Sep2010_final p105.pdf
reactionscheme_1 .cdx