Water → N-(3,4,5-Trimethoxyphenyl)biphenyl-3-sulfonamide

HRID 70040Notes

Reaction equation

HRID 70040 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[C:3]([S:7](Cl)(=[O:9])=[O:8])[CH:2]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:23]=[C:24]([O:28][CH3:29])[C:25]=1[O:26][CH3:27])[NH2:22].C(N(CC)CC)C.O>CN(C=O)C>[CH3:29][O:28][C:24]1[CH:23]=[C:21]([NH:22][S:7]([C:3]2[CH:2]=[C:1]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:6]=[CH:5][CH:4]=2)(=[O:9])=[O:8])[CH:20]=[C:19]([O:18][CH3:17])[C:25]=1[O:26][CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 322853,4,5-TrimethoxyanilineHCID 38027523-Phenylbenzene-1-sulfonyl chloride

Product 1

HCID 53363794N-(3,4,5-Trimethoxyphenyl)biphenyl-3-sulfonamideYield 91.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 65 mg of biphenyl-3-sulfonyl chloride (0.25 mmol), 44 mg of 3,4,5-trimethoxyaniline (0.24 mmol), and 0.3 mmol of triethylamine in 5 mL DMF was stirred overnight. The reaction mixture was treated with water and extracted with ethyl acetate. After a conventional workup, column chromatography (silica gel, petroleum ether/ethyl acetate) gave 88 mg compounds (4d) (91.7%). 1H NMR (500 MHz, CDCl3) δ 7.96 (t, 1H, J=1.8 Hz), 7.81-7.74 (m, 2H), 7.57-7.40 (m, 6H), 6.33 (s, 2H), 3.86 (s, 3H), 3.80 (s, 6H). MS (ESI) m/z 422.1 (M+Na)+.

Workup

  1. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-5ceb9119a1ea43b782f95bdd26dc728f
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Reaction notes

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