Acetic Acid → 3-[[3-(3,5-Dichlorophenyl)phenyl]sulfonylamino]benzoic acid

HRID 589724Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2[CH:21]=[C:22]([S:26](Cl)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=2)[CH:16]=[C:17]([Cl:19])[CH:18]=1.[Li+:30].[OH-].[CH3:32][C:33]([OH:35])=[O:34]>C1COCC1>[Cl:19][C:17]1[CH:16]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([S:26]([NH:1][C:2]3[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=3)[C:5]([O:7][CH3:8])=[O:6])(=[O:28])=[O:27])[CH:21]=2)[CH:14]=[C:13]([Cl:12])[CH:18]=1.[Cl:19][C:17]1[CH:16]=[C:15]([C:20]2[CH:21]=[C:22]([S:26]([NH:1][C:2]3[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=3)[C:5]([OH:7])=[O:6])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=2)[CH:14]=[C:13]([Cl:12])[CH:18]=1.[Li:30][O:34][C:33]([CH3:32])=[O:35]

Participants

Conditions

Temperature: 56 °C

Procedure

The intermediate methyl 3-{[(3′,5′-dichlorobiphenyl-3-yl)sulfonyl]amino}benzoate was synthesised according to the first step in General Procedure 2, described in Example 5, with methyl 3-aminobenzoate (7.55 mg, 0.05 mmol) and [3-(3,5-dichlorophenyl)phenyl]sulfonyl chloride (17.7 mg, 0.055 mmol). The ester intermediate was dissolved in aqueous THF (2 mL, 1:1 THF/water) and then LiOH (11 mg, 0.26 mmol, 6 equiv.) was added. The reaction mixture was stirred at 56° C. overnight. After addition of HOAc (15 the solvents were evaporated giving the title compound in a mixture with LiOAc. MS (ESI+) calcd for C19H13Cl2NO4S 420.994234, found 420.994364.

Workup

customwere evaporated

Sources & evidence

ORD record: ord-838c11eaba9d4f7ea665dee7761e6a52
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233946B2

Reaction notes

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