Hydrochloric Acid → Ethyl 2-[(6-chloronaphthalen-2-ylsulfonyl)amino]acetate

HRID 25037

Reaction equation

HRID 25037 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].C(N(CC)CC)C.[Cl:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([S:27](Cl)(=[O:29])=[O:28])[CH:21]=[CH:20]2.Cl>C(Cl)Cl>[Cl:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([S:27]([NH:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8])(=[O:29])=[O:28])[CH:21]=[CH:20]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 106351296-Chloronaphthalene-2-sulfonyl chloride

Product 1

HCID 23250750Ethyl 2-[(6-chloronaphthalen-2-ylsulfonyl)amino]acetateYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Glycine ethyl ester hydrochloride (9.88 g) was suspended in methylene chloride (500 ml), and triethylamine (20.2 ml) and then 6-chloronaphthalene-2-sulfonyl chloride (17.6 g) were added to the suspension under cooling with ice. After stirring at room temperature for 1 hour and adjusting the mixture to pH 2 by addition of 1N hydrochloric acid, the mixture was extracted with methylene chloride. The methylene chloride layer was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. After washing the resulting crystals in n-hexane, the crystals were collected by filtration and air-dried to obtain the title compound (22.4 g).

Workup

  1. temperatureunder cooling with ice
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe methylene chloride layer was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. washAfter washing the resulting crystals in n-hexane
  7. filtrationthe crystals were collected by filtration
  8. customair-dried

Sources & evidence

ORD record
ord-b5bd6018b5cd40e6af74684320baea73
Source dataset
uspto-grants-2005_02
Patent number
US06858599B2

Linked notes

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