Triethylamine → 4-(4-Morpholinylcarbonyl)phenyl trifluoromethanesulphonate

HRID 2179576Notes

Reaction equation

HRID 2179576 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[N:16]1([C:22]([C:24]2[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=2)=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(N(CC)CC)C>ClCCl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:27]1[CH:26]=[CH:25][C:24]([C:22]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:23])=[CH:29][CH:28]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 7586556(4-Hydroxyphenyl)(morpholino)methanone

Product 1

HCID 179828654-(4-Morpholinylcarbonyl)phenyl trifluoromethanesulphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

1.23 ml (7.24 mmol) of trifluoromethanesulphonic anhydride are slowly added dropwise to a solution, cooled to −10° C., of 1.0 g (4.83 mmol) of 4-(4-morpholinyl-carbonyl)phenol and 2.02 ml (14.48 mmol) of triethylamine in 20 ml of dichloromethane. The mixture is stirred at −10° C. for 30 min and then at 0° C. for 30 min. It is washed successively with 10% strength sodium bicarbonate solution, water and saturated sodium chloride solution, dried over sodium sulphate and concentrated in vacuo, and the residue is dried under high vacuum. 1.71 g (94.6% of theory) of the title compound are obtained.

Workup

  1. waitat 0° C. for 30 min
  2. washIt is washed successively with 10% strength sodium bicarbonate solution, water and saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customthe residue is dried under high vacuum

Sources & evidence

ORD record
ord-66153291ff8e40ba9b726c9882f793e3
Source dataset
uspto-grants-2015_06
Patent number
US09067931B2

Reaction notes

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