Benzoic acid, 3-amino-, methyl ester → Methyl 3-{[(2,5-difluorophenyl)sulfonyl]amino}benzoate

HRID 1961731Notes

Reaction equation

HRID 1961731 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].[F:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[F:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[S:20]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 78274Benzoic acid, 3-amino-, methyl esterHCID 27369112,5-Difluorobenzenesulfonyl chloride

Product 1

HCID 16344470Methyl 3-{[(2,5-difluorophenyl)sulfonyl]amino}benzoateYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following a procedure analogous to the procedure described in Intermediate 5, Step A using methyl 3-aminobenzoate (16 g, 105.9 mmol) in DCM (150 mL) and 2,5-difluorobenzene-1-sulfonyl chloride (24.7 g, 116.5 mmol) the title compound was obtained (25.6 g, 73.8% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.06-11.13 (br, 1H), 7.42-7.52 (m, 2H), 7.52-7.77 (m, 4H), 7.78-7.80 (m, 1H), 3.88 (s, 3H).

Sources & evidence

ORD record
ord-5c31d28097f64e74807c099b20f51bb4
Source dataset
uspto-grants-2013_04
Patent number
US08415345B2

Reaction notes

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