Water → HCID 9949854, compound

HRID 1276342Notes

Reaction equation

HRID 1276342 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][CH:20]=[C:19]1Cl.[CH3:24]S(O)(=O)=O.O>C(OCC)(=O)C.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:19]3[S:18][CH:22]=[CH:21][CH:20]=3)=[N:1][C:2]=2[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 72992-ChlorothiopheneHCID 22116138HCID 22116138, compound

Product 1

HCID 9949854HCID 9949854, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

This compound is prepared from 2-amino-4-chloro-6-[2-(pyridin-2-yl)ethyl]phenol and 2-thienyl chloride using method A, with ethyl acetate as solvent to give the crude amide in 99% yield. This is treated with methanesulphonic acid in toluene at reflux, with azeotropic removal of water to give the title compound, (31%) as a white crystalline solid after trituration and recrystallisation (EtOAc), m.p. 90-91° C. TLC (SiO2 ; EtOAc:hexanes 1:1, Rf=0.46). Mass Spectrum CI (methane), m/z=341 [M+H]+.

Workup

  1. customto give the crude amide in 99% yield

Sources & evidence

ORD record
ord-1047d4d4c87040f5823e4e4f8f9b3391
Source dataset
uspto-grants-2000_12
Patent number
US06166041

Reaction notes

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