Hydrochloric Acid → 2-[[4-Cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethyl methanesulfonate

HRID 1173405Notes

Reaction equation

HRID 1173405 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:17][C:18]([F:21])([F:20])[F:19])[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1.CCN(CC)CC.[CH3:29][S:30](Cl)(=[O:32])=[O:31].Cl>C(Cl)Cl>[CH3:29][S:30]([O:1][CH2:2][CH2:3][N:4]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:15])([F:16])[F:14])[CH:6]=1)[CH2:17][C:18]([F:19])([F:20])[F:21])(=[O:32])=[O:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 866237314-[(2-Hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

Product 1

HCID 866237322-[[4-Cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[(2-hydroxyethyl)(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.104 g, 0.333 mmol) in CH2Cl2 (3 mL) at 0° C. was added Et3N (0.07 mL, 0.5 mmol), followed by MsCl (0.03 mL, 0.37 mmol). The resulting mixture was stirred 12 h, gradually warming to rt. The mixture was poured into 10% v/v HCl and the layers were separated. The organic layer was washed (sat'd NaHCO3, water, brine), dried over Na2SO4, filtered and concentrated to a colorless film (0.122 g), which was used without further purification: 1H NMR (300 MHz, CDCl3) δ 7.71 (d, J=8.8 Hz, 1H), 7.12 (d, J=2.4 Hz, 1H), 6.99 (dd, J=8.7, 2.7 Hz, 1H), 4.43 (t, J=5.7 Hz, 2H), 4.10 (q, J=8.5 Hz, 2H), 3.95 (t, J=5.7 Hz, 2H), 3.02 (s, 3H).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed (sat'd NaHCO3, water, brine)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to a colorless film (0.122 g), which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-221e7007a04547d6a97f88a5814837cc
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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