Thionyl Chloride → HCID 131728715, compound

HRID 1367260Notes

Reaction equation

HRID 1367260 reaction equation
[C:1]([C:5]([C:8]([C:11]([S:14]([N:17]([CH2:19][CH2:20]I)[CH3:18])(=[O:16])=[O:15])([F:13])[F:12])([F:10])[F:9])([F:7])[F:6])([F:4])([F:3])[F:2].C(C(C(C(S(N(CCO)C)(=O)=O)(F)F)(F)F)(F)F)(F)(F)F.S(Cl)([Cl:45])=O>C(Cl)Cl>[C:1]([C:5]([C:8]([C:11]([S:14]([N:17]([CH2:19][CH2:20][Cl:45])[CH3:18])(=[O:16])=[O:15])([F:13])[F:12])([F:10])[F:9])([F:7])[F:6])([F:4])([F:3])[F:2]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 1186882-(N-(Perfluorobutylsulfonyl)-N-methylamino)ethanolHCID 131728716HCID 131728716, compound

Product 1

HCID 131728715HCID 131728715, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

CF3(CF2)3SO2N(Me)CH2CH2I was made as follows: CF3(CF2)3SO2N(Me)CH2CH2OH was reacted with an excess of thionyl chloride in methylene chloride at 25-45° C. to give CF3(CF2)3SO2N(Me)CH2CH2Cl, which (7.1 g) was mixed with a solution of 6.0 g NaI in acetone. The resulting solution was stirred at reflux, and the conversion to CF3(CF2)3SO2N(Me)CH2CH2I was followed by GC. At 24 hours, conversion was 14 percent, and 6.0 g more NaI was added; at 3 days, conversion was 46 percent; at 6 days, conversion was 72 percent, and 6.0 g NaI was added; at 13 days, 96 percent conversion was achieved. The resulting product was precipitated with water and recrystallized from hexane to provide 6.2 g white plates with a m.p. of 80-82° C. FO2S(CF2)2O(CF2)2I was obtained from Sigma-Aldrich Chemical Company, St. Louis, Mo. C3F6O(isoC3F3O)5CF(CF3) can be prepared essentially as described by Chen et. al. in J Fluorine Chem. 65, 59 (1993). I(CF2)4I was obtained from Sigma-Aldrich Chemical Company, St. Louis, Mo. CF3(CF2)7Br was obtained from 3M Company, St. Paul, Minn., and is available from Sigma-Aldrich Chemical Company, St. Louis, Mo. Sodium acetate was obtained from Sigma-Aldrich Chemical Company, St. Louis, Mo. Dimethylsulfoxide (DMSO) was obtained from Alfa Aesar, Ward Hill, Mass. Tetrahydrofuran (THF) was obtained from EMD Chemicals, Inc., Gibbstown, N.J. p-Toluenesulfonic acid was obtained from J. T. Baker, Phillipsburg, N.J. NaHCO3 was obtained from EMD Chemicals, Inc., Gibbstown, N.J.

Sources & evidence

ORD record
ord-03d3613b32f2415099272bee640faeae
Source dataset
uspto-grants-2011_02
Patent number
US07893186B2

Reaction notes

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