4-Toluenesulfonyl chloride → HCID 12967767, compound

HRID 411742Notes

Reaction equation

HRID 411742 reaction equation
Cl.[CH:2]1([C:11]([OH:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][NH:3]1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:24][C:14]1[CH:19]=[CH:18][C:17]([S:20]([N:3]2[CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:2]2[C:11]([OH:13])=[O:12])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 133813702,3-Dihydro-1H-isoindole-1-carboxylic acid--hydrogen chloride (1/1)

Product 1

HCID 12967767HCID 12967767, compoundYield 7.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1,3-Dihydro-2H-isoindole-1-carboxylic acid, hydrochloride (0.31 g, 1.9 mmol), p-toluenesulfonyl chloride (0.4 g, 2.09 mmol), and Na2CO3 (0.403 g, 3,8 mmol) were dissolved in water (4 mL). The reaction mixture was stirred at rt for 20 hr. The residue was dissolved in water and washed with EtOAc. The aqueous layer was acidified with concentrated HCl and extracted with CH2Cl2 (2X). The organic layers were dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by HPLC to give N-[4-methylbenzenesulfonyl]-1,3-dihydro-2H-isoindole-1-carboxylic acid (0.047 g). MS m/e 318.1 (M+)

Workup

  1. washwashed with EtOAc
  2. extractionextracted with CH2Cl2 (2X)
  3. dry with materialThe organic layers were dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-f584de7c809a4386bcad26607725e91f
Source dataset
uspto-grants-2003_05
Patent number
US06559174B2

Reaction notes

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