4-ethyl-N-(2-methylpropyl)aniline → methyl 2-bromo-5-(N-(4-ethylphenyl)-N-isobutylsulfamoyl)benzoate

HRID 1746430Notes

Reaction equation

[CH2:1]([C:3]1[CH:13]=[CH:12][C:6]([NH:7][CH2:8][CH:9]([CH3:11])[CH3:10])=[CH:5][CH:4]=1)[CH3:2].[Br:14][C:15]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18]>N1C=CC=CC=1>[Br:14][C:15]1[CH:24]=[CH:23][C:22]([S:25](=[O:27])(=[O:26])[N:7]([C:6]2[CH:12]=[CH:13][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[CH2:8][CH:9]([CH3:10])[CH3:11])=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 4-ethyl-N-isobutylaniline (400 mg, 2.256 mmol) in pyridine (2 mL) was added methyl 2-bromo-5-(chlorosulfonyl)benzoate (707 mg, 2.256 mmol) portionwise, over 30 minutes. The reaction mixture was stirred at 20° C. for 30 minutes then stood at room temperature, in air, for 16 hours. The solvent was evaporated in vacuo to give a crude yellow solid. The crude was then triturated with methanol, filtered and dried in vacuo to give the desired product (600 mg) as a white solid. LCMS (M+1) 454/456, RT 1.41 mins.

Workup

waitthen stood at room temperature, in air, for 16 hours
customThe solvent was evaporated in vacuo
customto give a crude yellow solid
customThe crude was then triturated with methanol
filtrationfiltered
customdried in vacuo

Sources & evidence

ORD record: ord-470b04b1a48b43ba866ce3fb82262ce6
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150508B2

Reaction notes

Loading…