Triethylamine → HCID 131726747, compound

HRID 2052755Notes

Reaction equation

HRID 2052755 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=[N:4][OH:5].Cl[CH2:17][CH2:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C.[Na+].[C:31]1([CH3:40])[CH:36]=[CH:35][C:34]([S:37]([O-:39])=[O:38])=[CH:33][CH:32]=1>C1COCC1.CN(C)C=O.O>[C:31]1([CH3:40])[CH:36]=[CH:35][C:34]([S:37]([CH2:17][CH2:18][S:19]([OH:21])(=[O:5])=[O:20])(=[O:39])=[O:38])=[CH:33][CH:32]=1.[F:1][C:2]([F:14])([F:15])[C:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=[N:4][OH:5]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 2723791Sodium p-toluenesulfinateHCID 59115151N-[2,2,2-Trifluoro-1-(4-methoxyphenyl)ethylidene]hydroxylamine

Product 1

HCID 131726747HCID 131726747, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In 40 mL of THF are dissolved 4.38 g (20.0 mmol) of 2,2,2-Trifluoro-1-(4-methoxyphenyl)-ethanone oxime and the solution is cooled in an ice-bath. To the solution are added successively 2-chloroethanesulfonyl chloride (2.3 mL, 22.0 mmol) and triethylamine (6.4 mL, 46.0 mmol), and the reaction solution is stirred at 0° C. for 1 h. Then, p-toluenesulfinic acid sodium salt (3.56 g, 20.0 mmol) in dimethylformamide (DMF) (80 mL) is added and the reaction solution is stirred at room temperature for 0.5 h. After the reaction mixture is poured into water, the crude product is extracted with ethyl acetate twice, washed with water, dried over MgSO4 and concentrated. The residue is purified by recrystallization from ethanol/toluene to afford the product as white solid. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 2.49 (s, 3H), 3.53 (t, 2H), 3.77 (t, 2H), 3.88 (s, 3H), 7.00 (d, 2H), 7.42 (d, 2H), 7.50 (d, 2H), 7.80 (d, 2H). mp. 157-158° C.

Workup

  1. temperaturethe solution is cooled in an ice-bath
  2. stirringthe reaction solution is stirred at room temperature for 0.5 h
  3. extractionthe crude product is extracted with ethyl acetate twice
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is purified by recrystallization from ethanol/toluene

Sources & evidence

ORD record
ord-2d7516a692d3497faddf7604a2541462
Source dataset
uspto-grants-2008_02
Patent number
US07326511B2

Reaction notes

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