Tetrahydrofuran → HCID 86610222, compound

HRID 2411122Notes

Reaction equation

HRID 2411122 reaction equation
O1CCCC1.[F:6][C:7]([F:31])([F:30])[C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[NH:18][C:19](=[O:29])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N:26]=[C:27]=[O:28])[CH:21]=1.[F:32][C:33]([F:40])([C:36]([F:39])([F:38])[F:37])[CH2:34][OH:35].C(N(CC)CC)C>C(OCC)(=O)C>[F:6][C:7]([F:30])([F:31])[C:8]1[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:11]=[CH:10][C:9]=1[NH:18][C:19](=[O:29])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:27]([O:35][CH2:34][C:33]([F:40])([F:32])[C:36]([F:39])([F:38])[F:37])=[O:28])[CH:21]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 98722,2,3,3,3-PentafluoropropanolHCID 86610220HCID 86610220, compound

Product 1

HCID 86610222HCID 86610222, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

First, to an anhydrous tetrahydrofuran solution (15 ml) of 0.5 g of N-(2,4-bistrifluoromethylphenyl) 3-isocyanatobenzamide produced in Example 10-1 were added 0.40 g of 2,2,3,3,3-pentafluoro-n-propanol and 0.13 g of triethylamine, and the resultant mixture was stirred at room temperature for 5 hours. The mixture was diluted with ethyl acetate (20 ml), and an organic layer was washed with a 1N sodium hydroxide aqueous solution and 1N hydrochloric acid. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1) to obtain 0.49 g (yield 70%) of the title compound.

Workup

  1. washan organic layer was washed with a 1N sodium hydroxide aqueous solution and 1N hydrochloric acid
  2. distillationThe solvent was distilled off under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-0ecdc347fda3463faf11c039ec01adf6
Source dataset
uspto-grants-2014_08
Patent number
US08816128B2

Reaction notes

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