Hydrochloric Acid → HCID 14457726, compound

HRID 2253683Notes

Reaction equation

HRID 2253683 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH2:7][CH2:8][C:9]([OH:11])=[O:10].[Cl:12][C:13]1[C:14]([S:24](Cl)(=[O:26])=[O:25])=[CH:15][C:16]2[C:21]([CH:22]=1)=[CH:20][C:19]([Cl:23])=[CH:18][CH:17]=2.Cl>O.O1CCOCC1>[Cl:12][C:13]1[C:14]([S:24]([NH:7][CH2:8][C:9]([OH:11])=[O:10])(=[O:26])=[O:25])=[CH:15][C:16]2[C:21]([CH:22]=1)=[CH:20][C:19]([Cl:23])=[CH:18][CH:17]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 11430Potassium CarbonateHCID 14457725HCID 14457725, compound

Product 1

HCID 14457726HCID 14457726, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of potassium carbonate (11.7 g) and glycine (6.4 g) in water (140 ml) were added 3,6-dichloronaphthalen-2-ylsulfonyl chloride (20.8 g) and dioxane (50 ml) at room temperature, and the mixture was stirred under reflux for 2 hours. After cooling to room temperature, the resultant solution was acidified with 2 N hydrochloric acid to a pH in the range of 1 to 2, and extracted with ethyl acetate. The organic layer was washed with water, then with saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate. Ethyl acetate was removed in vacuo to give 19.0 g of the objective compound.

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialwith saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate
  5. customEthyl acetate was removed in vacuo

Sources & evidence

ORD record
ord-16d97900a2e04bd38e63d3d953ee79db
Source dataset
uspto-grants-1993_08
Patent number
US05232936

Reaction notes

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