Sodium Hydroxide → HCID 66755708, compound

HRID 1642129Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH:13]2[C:21]([O:23]C)=[O:22])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].CO.O1CCOCC1.[OH-].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH:13]2[C:21]([OH:23])=[O:22])(=[O:10])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Reactant 3

HCID 14798Sodium Hydroxide

HCID 21966525Dioxane Methanol

HCID 66755963HCID 66755963, compound

Product 1

HCID 66755708HCID 66755708, compound

Procedure

Methyl 1-(3,4-dichlorophenylsulfonyl)indoline-2-carboxylate (49.8 g, 128.92 mmol) was dissolved in a mixture of methanol/dioxane/4 M NaOH (15/4/1, 960 ml, 193.38 mmol NaOH, 1.5 eq.), and further 4 M NaOH (145 ml, 580.14 mmol, 4.5 eq.) was added thereto. The solution was stirred overnight at room temperature and then concentrated using a rotary evaporator. Ethyl acetate was added to the residue, and the mixture was washed with 0.5 M KHSO4. The aqueous phase was then extracted three times with ethyl acetate, and the combined organic phases were washed with saturated NaCl solution (500 ml), dried (sodium sulfate) and concentrated in vacuo. The residue was washed with diethyl ether, filtered and dried.

Workup

additionwas added
concentrationconcentrated
customa rotary evaporator
additionEthyl acetate was added to the residue
washthe mixture was washed with 0.5 M KHSO4
extractionThe aqueous phase was then extracted three times with ethyl acetate
washthe combined organic phases were washed with saturated NaCl solution (500 ml)
dry with materialdried (sodium sulfate)
concentrationconcentrated in vacuo
washThe residue was washed with diethyl ether
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-381f059163f6498dba6f466a4ff460dc
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119633B2

Reaction notes

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