Ethanesulfonylchloride, 2-chloro- → HCID 56655832, compound

HRID 1622772Notes

Reaction equation

Cl[CH2:2][CH2:3][S:4](Cl)(=[O:6])=[O:5].[H-].[Na+].[CH3:10][C:11]1[CH:30]=[CH:29][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:23]([NH2:28])=[N:24][CH:25]=[CH:26][CH:27]=3)=[CH:18][CH:17]=2)=[CH:13][CH:12]=1>C1COCC1>[CH3:10][C:11]1[CH:12]=[CH:13][C:14]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[C:23]4=[N:28][S:4](=[O:6])(=[O:5])[CH2:3][CH2:2][N:24]4[CH:25]=[CH:26][CH:27]=3)=[CH:18][CH:17]=2)=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-Chloroethanesulfonyl chloride (19.5 mL) was added dropwise to a mixture of NaH (60%, 12.5 g) in THF (100 mL) at 0° C. in an ice bath. After being stirred at 0° C. for 10 min, a solution of 3-[4-(4-methylphenoxy)phenyl]pyridin-2-amine (17.2 g) in THF (100 mL) was added dropwise to the mixture at 0° C. The ice-bath was removed and the mixture was stirred at room temperature under N2 for 14 hr. The mixture was quenched with EtOH at 0° C. and water was added dropwise to the mixture at 0° C. The mixture was stirred at room temperature for 1 h. The precipitate was collected by filtration, and washed with water and EtOAc to give the title compound (8.68 g) as colorless powder.

Workup

customThe ice-bath was removed
stirringthe mixture was stirred at room temperature under N2 for 14 hr
customThe mixture was quenched with EtOH at 0° C.
additionwater was added dropwise to the mixture at 0° C
stirringThe mixture was stirred at room temperature for 1 h
filtrationThe precipitate was collected by filtration
washwashed with water and EtOAc

Sources & evidence

ORD record: ord-5cad608730f84f69bff838d0070eafe3
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778934B2

Reaction notes

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