Water → HCID 67305472, compound

HRID 1009461Notes

Reaction equation

HRID 1009461 reaction equation
[Cl:1][C:2]1[C:3]([CH3:19])=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.BrCC(O[CH2:25][CH3:26])=O.[C:27](=[O:30])([O-])[O-:28].[K+].[K+].O.[CH3:34]N(C=O)C>>[CH2:25]([CH:26]([C:27]([OH:28])=[O:30])[N:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH3:19])[S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)(=[O:10])=[O:11])[CH3:34]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 3450994HCID 3450994, compound

Product 1

HCID 67305472HCID 67305472, compound

Conditions

Temperature
100 °C

Procedure

34.5 g of N-(3-chloro-2-methylphenyl)-4-methylbenzenesulfonamide was dissolved in 232 mL of DMF, and 21.4 g of ethyl bromoacetate and 19.3 g of potassium carbonate were added thereto, followed by stirring at 100° C. for 1 hour. The reaction liquid was cooled to room temperature, and then water was added, followed by extraction with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20) to obtain 34.6 g of ethyl N-(3-chloro-2-methylphenyl)-N-[(4-methylphenyl)sulfonyl]glycine.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=80:20)

Sources & evidence

ORD record
ord-5436fa672e284b229315c24a26f71c4a
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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