4-(Chlorosulfonyl)benzoic acid → 4-[[(2-Methoxyphenyl)methylamino]sulfonyl]benzoic acid

HRID 1482822Notes

Reaction equation

HRID 1482822 reaction equation
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[NH:18][CH3:19]>>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[N:18]([CH3:19])[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

3

Reactant 2

HCID 823854-(Chlorosulfonyl)benzoic acidHCID 27595792-Methoxy-N-methylaniline

Product 1

HCID 23601994-[[(2-Methoxyphenyl)methylamino]sulfonyl]benzoic acid

Procedure

4-(chlorosulfonyl)benzoic acid (500 mg, 2.27 mmol) was treated with 2-methoxy-N-methylaniline (933 mg, 6.8 mmol) using method A to give 4-(N-(2-methoxyphenyl)-N-methylsulfamoyl)benzoic acid as an off white solid. Yield: 515 mg (71%). 1H-NMR: 8.11 (d, J=8.5 Hz, 2H), 7.73 (d, J=8.5 Hz, 2H), 7.33 (ddd, J=8.5, 7.5, 1.5 Hz, 1H), 7.17 (dd, J=7.5, 1.5 Hz, 1H), 7.00-6.92 (m, 2H), 3.33 (s, 3H), 3.14 (s, 3H).

Sources & evidence

ORD record
ord-c113df7c78f943fa9d81b716c0bc9506
Source dataset
uspto-grants-2016_08
Patent number
US09416101B2

Reaction notes

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