Water → HCID 9905971, compound

HRID 1276343Notes

Reaction equation

HRID 1276343 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[CH:22]=[CH:21][C:20](Cl)=[CH:19]1.[CH3:24]S(O)(=O)=O.O>O1CCOCC1.C1(C)C=CC=CC=1>[Cl:8][C:6]1[CH:5]=[C:4]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[C:3]2[O:17][C:24]([C:20]3[CH:21]=[CH:22][S:18][CH:19]=3)=[N:1][C:2]=2[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 870173-ChlorothiopheneHCID 22116138HCID 22116138, compound

Product 1

HCID 9905971HCID 9905971, compoundYield 30%

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 3-thienyl chloride using method A with 1,4-dioxan as solvent to give the crude amide in a 100% yield. This is treated with methanesulphonic acid in toluene at reflux, with azeotropic removal of water. Purification by flash chromatography (SiO2, EtOAc:hexanes 1:1), gave the title compound, (30%) as a white crystalline solid, m.p. 126-127° C. TLC (SiO2, EtOAc:hexanes 1:1, Rf=0.46). CI Mass Spectrum (methane), m/z=341 [M+H]+.

Workup

  1. customto give the crude amide in a 100% yield
  2. customPurification by flash chromatography (SiO2, EtOAc:hexanes 1:1)

Sources & evidence

ORD record
ord-1b5db37a9e1041fb93f0dcb9d1bcd0c5
Source dataset
uspto-grants-2000_12
Patent number
US06166041

Reaction notes

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