Hydrochloric Acid → HCID 59704780, compound

HRID 1716312Notes

Reaction equation

HRID 1716312 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27].Cl>C(Cl)Cl.C(Cl)Cl.O>[F:1][C:2]([F:17])([F:18])[C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([NH:14][S:26]([CH3:25])(=[O:28])=[O:27])=[CH:12][CH:13]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 27607514-(4-(Trifluoromethyl)phenoxy)aniline

Product 1

HCID 59704780HCID 59704780, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21908982Water methylene chlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(4-trifluoromethyl-phenoxy)-phenylamine (15.18 g, 60 mmol) and pyridine (7.2 mL, 90 mmol) in dried CH2Cl2 (100 mL) under N2 at 0° C. was added methanesulfonyl chloride (5.22 mL, 66 mmol) dropwise. The mixture was stirred at 0° C. for 1 h and was then poured into CH2Cl2/H2O (100 mL/100 mL). 2N HCl(aq) (30 mL) was added into additional funnel. The organic layer was then washed with H2O (100 mL), brine (100 mL), dried (Na2SO4), and filtered. After removal of solvent, the crude product can be resolidified from Et2O/hexane to give 18.2 g of the titled product (92%) as a pale brown solid. 1H NMR (300 MHz, CDCl3) δ 7.58 (d, J=9.0 Hz, 2H), 7.30 (d, J=9.0 Hz, 2H), 7.04 (d, J=9.0 Hz, 4H), 6.93 (s, 1H, NH), 3.04 (s, 3H); MS (EI) 331 (M+), 330 (M+−1, 100).

Workup

  1. washThe organic layer was then washed with H2O (100 mL), brine (100 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customAfter removal of solvent

Sources & evidence

ORD record
ord-c7b3b9c68f1a4f8d8c942d618958d013
Source dataset
uspto-grants-2010_09
Patent number
US07803793B2

Reaction notes

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