Water → HCID 15078392, compound

HRID 1110438Notes

Reaction equation

HRID 1110438 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:12][CH2:13][C:14]([O:16]C)=[O:15])[CH:9]=2)[CH2:4]1.O.C(=O)([O-])[O-].[K+].[K+].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(OCC)(=O)C>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:2][CH:3]2[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([O:12][CH2:13][C:14]([OH:16])=[O:15])[CH:9]=3)[CH2:4]2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 86744373HCID 86744373, compound

Product 1

HCID 15078392HCID 15078392, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

2.71 g of methyl (2-aminoindan-5-yl)oxyacetate hydrochloride are added to a mixture of 80 ml of ethyl acetate, 40 ml of water and 415 mg of potassium carbonate and a solution of 2.11 g of 4-chlorophenylsulfonyl chloride in 40 ml of ethyl acetate is added dropwise thereto. The mixture is stirred for 2 hours and the ethyl acetate layer is separated. The ethyl acetate layer is washed successively with an aqueous 10% hydrochloric acid solution, an aqueous saturated sodium bicarbonate solution and an aqueous sodium chloride solution, dried and evaporated to remove solvent. 30 ml of methanol and 20 ml of 1N sodium hydroxide solution are added to the residue and the mixture is stirred at room temperature for 20 minutes. The reaction mixture is adjusted to pH 1 with an aqueous 10% hydrochloric acid solution and extracted with a mixture of chloroform and tetrahydrofuran. The extract is dried and evaporated to remove solvent. The residue is recrystallized from tetrahydrofuran-n-hexane-isopropyl ether to give 3.57 g of {2-[(4-chlorophenyl)sulfonylamino]indan-5-yl}oxyacetic acid as yellow prisms. Yield: 94% m.p. 170°-172° C.

Workup

  1. customthe ethyl acetate layer is separated
  2. washThe ethyl acetate layer is washed successively with an aqueous 10% hydrochloric acid solution
  3. dry with materialan aqueous saturated sodium bicarbonate solution and an aqueous sodium chloride solution, dried
  4. customevaporated
  5. customto remove solvent
  6. addition30 ml of methanol and 20 ml of 1N sodium hydroxide solution are added to the residue
  7. stirringthe mixture is stirred at room temperature for 20 minutes
  8. extractionextracted with a mixture of chloroform and tetrahydrofuran
  9. customThe extract is dried
  10. customevaporated
  11. customto remove solvent
  12. customThe residue is recrystallized from tetrahydrofuran-n-hexane-isopropyl ether

Sources & evidence

ORD record
ord-7b9e5eab302f4d24b2ffc19ef01e1a80
Source dataset
uspto-grants-1990_12
Patent number
US04975460

Reaction notes

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