5-(4-Bromophenyl)-4,6-dichloropyrimidine → N-[5-(4-Bromophenyl)-6-chloro-4-pyrimidinyl]-N'-(phenylmethyl)sulfamide

HRID 2189131Notes

Reaction equation

HRID 2189131 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([Cl:15])=[N:10][CH:11]=[N:12][C:13]=2Cl)=[CH:4][CH:3]=1.[K+].[CH2:17]([NH:24][S:25]([NH-:28])(=[O:27])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CS(C)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl:15][C:9]1[N:10]=[CH:11][N:12]=[C:13]([NH:28][S:25](=[O:26])(=[O:27])[NH:24][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 197352625-(4-Bromophenyl)-4,6-dichloropyrimidineHCID 21041359Benzylsulfamide potassium salt

Product 1

HCID 21041369N-[5-(4-Bromophenyl)-6-chloro-4-pyrimidinyl]-N'-(phenylmethyl)sulfamideYield 102.7%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5-(4-bromophenyl)-4,6-dichloro-pyrimidine (4.00 g, 13.2 mmol) and benzylsulfamide potassium salt (7.38 g, 32.9 mmol) in DMSO (30 mL) was stirred at it for 24 h before being diluted with a 10% aq. citric acid solution (200 mL). The suspension that formed was filtered. The collected solid was washed well with water and dried under HV at 40° C. for 48 h to give the expected product as a white powder (6.15 g).

Workup

  1. customThe suspension that formed
  2. filtrationwas filtered
  3. washThe collected solid was washed well with water
  4. customdried under HV at 40° C. for 48 h

Sources & evidence

ORD record
ord-73ff0b429ec240c1b25da5e1ff581dd3
Source dataset
uspto-grants-2012_12
Patent number
US08324232B2

Reaction notes

Loading…