4-Toluenesulfonyl chloride → HCID 24805800, compound

HRID 522724Notes

Reaction equation

HRID 522724 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:7][CH2:6][C:3]2([C:2]([F:9])([F:8])[F:1])[CH2:5][CH2:4]2)(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 509906611-(Trifluoromethyl)cyclopropanemethanol

Product 1

HCID 24805800HCID 24805800, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Treat a solution of (1-(trifluoromethyl)cyclopropyl)methanol (7 g, 50 mmol) and 4-methylbenzene-1-sulfonyl chloride (10.4 g, 55 mmol) in anhydrous DCM (100 mL) with TEA (10 g, 100 mmol) and N,N-dimethylpyridin-4-amine (0.6 g, 5 mmol). Stir at RT overnight. Wash the mixture successively with HCl (2M), saturated NaHCO3, and brine, dry over Na2SO4 and concentrate under reduced pressure to give the title compound (12 g, 81% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.79 (d, J=8.0 Hz, 2H), 7.50 (d, J=8.0 Hz, 2H), 4.13 (s, 2H), 2.43 (s, 3H), 1.08-1.05 (m, 2H), 0.96-0.94 (m, 2H).

Workup

  1. washWash the mixture successively with HCl (2M), saturated NaHCO3, and brine
  2. dry with materialdry over Na2SO4
  3. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-63256913ff1c41ef8d238a774484e5cc
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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