Cyanuric chloride → 4-tert-butyl-N-methyl-N-(3-(aminosulfonyl)phenyl)benzamide

HRID 79099Notes

Reaction equation

[C:1]([C:5]1[CH:24]=[CH:23][C:8]([C:9]([N:11]([C:13]2[CH:14]=[C:15]([S:19](O)(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=2)[CH3:12])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:25]1C(Cl)=NC(Cl)=NC=1Cl.C(N(CC)CC)C.[OH-].[NH4+]>CC(C)=O>[C:1]([C:5]1[CH:24]=[CH:23][C:8]([C:9]([N:11]([CH3:12])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([NH2:25])(=[O:21])=[O:20])[CH:14]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 3-(4-tert-butyl-N-methylbenzamido)benzenesulfonic acid (12 mg, 35 μmol), cyanuric chloride (7.0 mg, 40 μmol), and triethylamine (6.0 μL, 40 μmol) in acetone (0.5 mL) was sealed in a glass tube and heated in a microwave oven at 120° C. for 10 min. Concentrated ammonium hydroxide (150 μL) was added, and the reaction was stirred for 6 h. The reaction was filtered, and the filtrate was purified by preparative reverse phase HPLC using 10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA) to give 4-tert-butyl-N-methyl-N-(3-(aminosulfonyl)phenyl)benzamide. LC/MS: m/z 347.3 (M+H)+ at 2.86 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

filtrationThe reaction was filtered
customthe filtrate was purified by preparative reverse phase

Sources & evidence

ORD record: ord-0cf14ec331364fe0a309edd917005dbb
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841483B2

Reaction notes

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