Potassium Carbonate → Ethyl (N-methyl-3-trifluoromethylbenzylsulfonamido)acetate

HRID 476519Notes

Reaction equation

HRID 476519 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[CH2:6][S:7](Cl)(=[O:9])=[O:8].[CH2:16]([O:18][C:19](=[O:23])[CH2:20][NH:21][CH3:22])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:22][N:21]([CH2:20][C:19]([O:18][CH2:16][CH3:17])=[O:23])[S:7]([CH2:6][C:5]1[CH:11]=[CH:12][CH:13]=[C:3]([C:2]([F:15])([F:14])[F:1])[CH:4]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 95849Glycine, N-methyl-, ethyl esterHCID 27946463-(Trifluoromethyl)phenylmethanesulfonyl chloride

Product 1

HCID 15118078Ethyl (N-methyl-3-trifluoromethylbenzylsulfonamido)acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

In this example, 22 g of 3-trifluoromethylbenzylsulfonyl chloride was added cautiously to a solution containing 27 g of the hydrochloride salt of sarcosine ethyl ester and 12 g of potassium carbonate in 90 ml of water at room temperature. The reaction mixture was heated to about 70° C. and maintained at this temperature for about four hours. The mixture was allowed to cool and then extracted with ethyl ether. The ethyl ether extract was dried over magnesium sulfate, filtered, and evaporated to dryness yielding 9.5 g of the title compound as an off-white solid.

Workup

  1. temperaturemaintained at this temperature for about four hours
  2. temperatureto cool
  3. extractionextracted with ethyl ether
  4. extractionThe ethyl ether extract
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-83bc17cc94464749af416e1a13827d0e
Source dataset
uspto-grants-1989_12
Patent number
US04885027

Reaction notes

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