Water → HCID 9952370, compound

HRID 1276344Notes

Reaction equation

HRID 1276344 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[C:3]=1[OH:17].[S:18]1[C:22]([C:23](Cl)=O)=[CH:21][C:20]2[CH:26]=[CH:27][CH:28]=[CH:29][C:19]1=2.CS(O)(=O)=O.O>O1CCOCC1.C1(C)C=CC=CC=1>[S:18]1[C:22]([C:23]2[O:17][C:3]3[C:4]([CH2:9][CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=4)=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[N:1]=2)=[CH:21][C:20]2[CH:26]=[CH:27][CH:28]=[CH:29][C:19]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 142384Benzo[b]thiophene-2-carbonyl ChlorideHCID 22116138HCID 22116138, compound

Product 1

HCID 9952370HCID 9952370, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

This compound is prepared from 2-amino-4-chloro-6-[2-(pyridin-2-yl)ethyl]-phenol and benzo[b]thiophene-2-carbonyl chloride using method A with 1,4-dioxan as solvent to give the crude amide (73%). This is treated with methanesulphonic acid in toluene at reflux with azeotropic removal of water to give the title compound, (41%) as a white crystalline solid m.p.=183-184° C. TLC (SiO2, EtOAc:hexanes 1:1, Rf=0.56). CI Mass Spectrum (methane) m/z=391 [M+H]+.

Workup

  1. customto give the crude amide (73%)

Sources & evidence

ORD record
ord-207f9d94bf894bd8b7974625545a2614
Source dataset
uspto-grants-2000_12
Patent number
US06166041

Reaction notes

Loading…