Citric Acid → N-[6-chloro-5-(2-chloro-5-methoxy-phenoxy)-pyrimidin-4-yl]-5-isopropyl-pyridine-sulphonamide

HRID 356649Notes

Reaction equation

HRID 356649 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[Cl:17])=[C:6]([Cl:18])[N:5]=[CH:4][N:3]=1.[CH:19]([C:22]1[CH:23]=[CH:24][C:25]([S:28]([NH2:31])(=[O:30])=[O:29])=[N:26][CH:27]=1)([CH3:21])[CH3:20].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CS(C)=O>[Cl:18][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:31][S:28]([C:25]2[CH:24]=[CH:23][C:22]([CH:19]([CH3:21])[CH3:20])=[CH:27][N:26]=2)(=[O:30])=[O:29])[C:7]=1[O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[Cl:17]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 181841935-Isopropylpyridine-2-sulfonamideHCID 219795664,6-Dichloro-5-(2-chloro-5-methoxy-phenoxy)-pyrimidine

Product 1

HCID 18938912N-[6-chloro-5-(2-chloro-5-methoxy-phenoxy)-pyrimidin-4-yl]-5-isopropyl-pyridine-sulphonamideYield 53.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

306 mg of 4,6-dichloro-5-(2-chloro-5-methoxy-phenoxy)-pyrimidine, 320 mg of 5-isopropyl-2-pyridine-sulphonamide and 180 mg of K tert.butylate dissolved in 2 ml of DMSO were reacted at 90° C. for 3 hours. After cooling to room temperature the reaction medium was acidified with aqueous citric acid; the compound was extracted with ethyl acetate and, after distillation of the solvent, crystallized from ethanol. 250 mg of N-[6-chloro-5-(2-chloro-5-methoxy-phenoxy)-pyrimidin-4-yl]-5-isopropyl-pyridine-sulphonamide were obtained as white crystals with m.p. 174°-175° C.

Workup

  1. customwere reacted at 90° C. for 3 hours
  2. extractionthe compound was extracted with ethyl acetate
  3. distillationafter distillation of the solvent
  4. customcrystallized from ethanol

Sources & evidence

ORD record
ord-a64f9edbf272448ca2eee8ddd7ecc751
Source dataset
uspto-grants-1998_11
Patent number
US05837708

Reaction notes

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