Diisopropylethylamine → 2-[5-(2-Chloro-ethyl)-2-methoxy-benzenesulfonylamino]-acetamide

HRID 2288961Notes

Reaction equation

HRID 2288961 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([S:10](Cl)(=[O:12])=[O:11])[CH:9]=1.Cl.[NH2:17][CH2:18][C:19]([NH2:21])=[O:20].C(N(CC)C(C)C)(C)C>O1CCOCC1.C(OCC)(=O)C>[Cl:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:14][CH3:15])=[C:8]([S:10]([NH:17][CH2:18][C:19]([NH2:21])=[O:20])(=[O:12])=[O:11])[CH:9]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2723639Glycinamide hydrochlorideHCID 187004055-(2-Chloro-ethyl)-2-methoxy-benzenesulfonyl chloride

Product 1

HCID 187004602-[5-(2-Chloro-ethyl)-2-methoxy-benzenesulfonylamino]-acetamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

5-(2-chloro-ethyl)-2-methoxy-benzenesulfonyl chloride (5.78 g, 21.5 mmol) is dissolved in dioxane (72 mL). To this solution is added glycinamide hydrochloride (4.75 g, 42.9 mmol) and N,N-diisopropylethylamine (7 mL, 42.9 mmol) with stirring at room temperature for 24 h. The solution is diluted with ethyl acetate (100 mL) and washed with 1 M H3PO4 (2×50 mL), sat NaHCO3, (1×50 mL,) brine (1×50 mL). The organic phase is dried with Na2SO4, filtered and the volatiles concentrated to a white solid. The solid is collected on a buchner by vacuum filtration and washed with ether to provide the title compound.

Workup

  1. washwashed with 1 M H3PO4 (2×50 mL)
  2. dry with materialThe organic phase is dried with Na2SO4
  3. filtrationfiltered
  4. concentrationthe volatiles concentrated to a white solid
  5. filtrationThe solid is collected on a buchner by vacuum filtration
  6. washwashed with ether

Sources & evidence

ORD record
ord-41e88732b71b4c16bc3c981d86d93864
Source dataset
uspto-grants-2000_07
Patent number
US06090825

Reaction notes

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