Water → Methyl [2-[(4-chlorophenyl)sulfonylamino]indan-5-yl]acetate

HRID 1086519Notes

Reaction equation

HRID 1086519 reaction equation
[ClH:1].[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=2)[CH2:4]1.C(=O)([O-])[O-].[K+].[K+].O.Cl[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31](Cl)(=[O:33])=[O:32]>C(OCC)(=O)C>[Cl:1][C:29]1[CH:28]=[CH:27][C:26]([S:31]([NH:2][CH:3]2[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=3)[CH2:4]2)(=[O:33])=[O:32])=[CH:25][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 761872-Chlorobenzenesulfonyl chlorideHCID 23359670Methyl (2-aminoindan-5-yl)acetate hydrochloride

Product 1

HCID 53769737Methyl [2-[(4-chlorophenyl)sulfonylamino]indan-5-yl]acetateYield 79.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl (2-aminoindan-5-yl)acetate hydrochloride (2.43 g), potassium carbonate (5.52 g), water (60 ml), ethyl acetate (60 ml) and 4 chlorophenylsulfonyl chloride (2.11 g) is stirred at room temperature for one hour. The ethyl acetate layer is separated from the reaction mixture, washed with aqueous saline solution, dried, and distilled under reduced pressure to remove the solvent. The resulting crude product is recrystallized from a mixture of ethyl acetate and n-hexane to give methyl [2-[(4-chlorophenyl)sulfonylamino]indan-5-yl]acetate (3.02 g).

Workup

  1. customThe ethyl acetate layer is separated from the reaction mixture
  2. washwashed with aqueous saline solution
  3. customdried
  4. distillationdistilled under reduced pressure
  5. customto remove the solvent
  6. customThe resulting crude product is recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-ae444deb1d154f5a945eb9bc984b9fb9
Source dataset
uspto-grants-1991_07
Patent number
US05030652

Reaction notes

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