Methanesulfonamide → N-methanesulfonyl (3-trifluoromethylphenoxy)(4-chlorophenyl)acetamide

HRID 973188Notes

Reaction equation

HRID 973188 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][CH:7]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:8](Cl)=[O:9].[Na].[CH3:24][S:25]([NH2:28])(=[O:27])=[O:26]>O1CCCC1>[CH3:24][S:25]([NH:28][C:8](=[O:9])[CH:7]([O:6][C:5]1[CH:18]=[CH:19][CH:20]=[C:3]([C:2]([F:22])([F:21])[F:1])[CH:4]=1)[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 5360545SodiumHCID 121092354-Chloro-α-[3-(trifluoromethyl)phenoxy]benzeneacetyl chloride

Product 1

HCID 54399462N-methanesulfonyl (3-trifluoromethylphenoxy)(4-chlorophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

(3-Trifluoromethylphenoxy)(4-chlorophenyl)acetyl chloride (0.02 mole) in tetrahydrofuran (50 ml.) is added over a 15-minute period to a solution of the sodium salt of methanesulfonamide (2.5 g., 0.021 mole) in tetrahydrofuran (50 ml.) at 0°-5° C., under a nitrogen atmosphere. The mixture is stirred at 20° C. for 20 hours and then the solvent is evaporated under vacuum. The residue is dissolved in chloroform and the solution is extracted with water. The chloroform solution is dried over anhydrous magnesium sulfate, filtered and the solvent removed to afford N-methanesulfonyl (3-trifluoromethylphenoxy)(4-chlorophenyl)acetamide.

Workup

  1. customthe solvent is evaporated under vacuum
  2. dissolutionThe residue is dissolved in chloroform
  3. extractionthe solution is extracted with water
  4. dry with materialThe chloroform solution is dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-0bd7c8a44bae46cbb1d40663e8710c2c
Source dataset
uspto-grants-1977_10
Patent number
US04055592

Reaction notes

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