N-bromobutanimide → 4,6-Dichloro-5-(2-bromo-5-methoxyphenoxy)pyrimidine

HRID 1736397Notes

Reaction equation

HRID 1736397 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)=[C:6]([Cl:17])[N:5]=[CH:4][N:3]=1.[Br:18]N1C(=O)CCC1=O>C(O)(=O)C.C(OC(=O)C)(=O)C>[Cl:17][C:6]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([O:15][CH3:16])[CH:12]=[CH:13][C:14]=2[Br:18])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 194326534,6-Dichloro-5-(3-methoxyphenoxy)-pyrimidine

Product 1

HCID 194327284,6-Dichloro-5-(2-bromo-5-methoxyphenoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 21895370AcOH AcOAcSolvent

Procedure

By brominating 4,6-dichloro-5-(3-methoxyphenoxy)-pyrimidine with N-bromosuccinimide in acetic acid/acetic anhydride at 100° C. there was obtained 4,6-dichloro-5-(2-bromo-5-methoxyphenoxy)pyrimidine; therefrom with p-tert-benzenesulfonamide K there was obtained N-[5-(2-bromo-5-methoxyphenoxy)-6-chloropyrimidin-4-yl]-4-tert-butyl -benzenesulfonamide and therefrom with Na ethylene glycolate there was obtained p-tert-butyl-N-[5-(2-bromo-5-methoxyphenoxy)-6-(2-hydroxyethoxy)-4-pyrimidinyl]-benzenesulfonamide.

Workup

  1. customat 100° C.

Sources & evidence

ORD record
ord-09da501688104c919b167c6d3261e60a
Source dataset
uspto-grants-1996_07
Patent number
US05541186

Reaction notes

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