Trifluoroacetic acid → HCID 23150795, compound

HRID 2264131Notes

Reaction equation

HRID 2264131 reaction equation
[H-].[Na+].FC(F)CO.C([NH:12][S:13]([C:16]1[C:21]([I:22])=[CH:20][CH:19]=[CH:18][C:17]=1[F:23])(=[O:15])=[O:14])(C)(C)C.FC(F)(F)C(O)=O>O1CCCC1>[F:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([I:22])[C:16]=1[S:13]([NH2:12])(=[O:14])=[O:15]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 24758Sodium hydrideHCID 1361872,2-Difluoroethan-1-olHCID 23150788HCID 23150788, compound

Product 1

HCID 23150795HCID 23150795, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.64 g (26.57 mmol) of sodium hydride is introduced in 10 ml of dry tetrahydrofuran and this initial charge is slowly admixed at room temperature with 2.18 g (26.57 mmol) of 2,2-difluoroethanol. The reaction mixture is stirred at room temperature until the evolution of gas ceases. Thereafter 4.00 g (13.29 mmol) of 2-fluoro-6-iodo-benzenesulfonamide, obtained from the reaction of N-(tert-butyl)-2-fluoro-6-iodobenzenesulfonamide with trifluoroacetic acid in analogy to example A3, in solution in 20 ml of dry tetrahydrofuran, are added dropwise. This reaction mixture is exposed to a microwave energy of 100 watts at 150° C. for 30 min. Thereafter the pH is adjusted to 4-5 using 2 N hydrochloric acid and the mixture is partitioned in water/ethyl acetate, the organic phase being dried and evaporated. This gives 3.00 g (62% of theory) of 2-(2,2-difluoroethoxy)-6-iodobenzenesulfonamide.

Workup

  1. additionthis initial charge

Sources & evidence

ORD record
ord-d14e7abc52ad4373bab91561ee126db0
Source dataset
uspto-grants-2010_12
Patent number
US07855166B2

Reaction notes

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