2-Naphthalenesulfonyl chloride → HCID 23002621, compound

HRID 398328Notes

Reaction equation

HRID 398328 reaction equation
Cl.[NH2:2][CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])[CH2:4][C:5]([OH:7])=[O:6].[OH-].[Na+].[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[S:27](Cl)(=[O:29])=[O:28]>O1CCOCC1.O>[OH:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH:3]([NH:2][S:27]([C:18]1[CH:19]=[CH:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:17]=1)(=[O:29])=[O:28])[CH2:4][C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 14798Sodium Hydroxide2×HCID 69944422HCID 69944422, compound

Product 1

HCID 23002621HCID 23002621, compoundYield 44.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1.1 g of 3-amino-3-(2-hydroxyphenyl)propionic acid hydrochloride, prepared according to J. Agric. Food Chem., 1977, 25, 965, are dissolved in 25 ml of dioxane and 10 ml of 1N NaOH are added; 1.12 g of 2-naphthalenesulphonyl chloride are gradually added while maintaining the pH at 11.5-12 by addition of 1N NaOH. After stirring for 2 hours at RT, the reaction medium is diluted in water, washed with EtOAc (twice) and then acidified to pH=1.5-2 by addition of 6N HCl. The white precipitate formed is drained, washed with water and dried in order to obtain 0.82 g of the expected product, m.p.=190-200° C.

Workup

  1. temperaturewhile maintaining the pH at 11.5-12
  2. washwashed with EtOAc (twice) and
  3. additionthen acidified to pH=1.5-2 by addition of 6N HCl
  4. customThe white precipitate formed
  5. washwashed with water
  6. customdried in order

Sources & evidence

ORD record
ord-5661ba8f3ad44998812f7c58e1ce49f7
Source dataset
uspto-grants-2003_08
Patent number
US06610882B2

Reaction notes

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