Water → HCID 22219519, compound

HRID 1793944Notes

Reaction equation

HRID 1793944 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][C:5]=1[NH:13][C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].O.C(=O)([O-])[O-].[K+].[K+].[C:28]([C:30]1[CH:31]=[CH:32][C:33]([O:40][CH3:41])=[C:34]([S:36](Cl)(=[O:38])=[O:37])[CH:35]=1)#[N:29]>O1CCCC1>[C:28]([C:30]1[CH:31]=[CH:32][C:33]([O:40][CH3:41])=[C:34]([S:36]([NH:1][CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][C:7]([CH:10]([CH3:12])[CH3:11])=[CH:6][C:5]=2[NH:13][C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:38])=[O:37])[CH:35]=1)#[N:29]

Participants

6

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 115287515-Cyano-2-methoxybenzene-1-sulfonyl chlorideHCID 22219495HCID 22219495, compound

Product 1

HCID 22219519HCID 22219519, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.125 g of ethyl N-[2-(2-aminoethyl)-5-isopropylphenyl]oxalamate in tetrahydrofuran (4 mL)-water (2 mL) were added successively 0.149 g of potassium carbonate and 0.125 g 5-cyano-2-methoxybenzenesulfonyl chloride, and the mixture was stirred at room temperature for 14 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 0.21 g of ethyl N-[2-[2-(5-cyano-2-methoxybenzenesulfonylamino)ethyl]-5-isopropylphenyl]oxalamate.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water, and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-21928d6b104b41ebaa97947e88812d48
Source dataset
uspto-grants-2006_04
Patent number
US07022689B2

Reaction notes

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