4,6-Dichloro-5-(o-methoxyphenoxy)-2-methyl-pyrimidine → HCID 18184223, compound

HRID 1358348Notes

Reaction equation

HRID 1358348 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([CH3:18])[N:3]=1.[K+].[C:20]([C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH-:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1)([CH3:23])([CH3:22])[CH3:21]>CS(C)=O.O>[C:20]([C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH:33][C:2]2[C:7]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([CH3:18])[N:3]=2)(=[O:31])=[O:32])=[CH:26][CH:25]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 2

HCID 219795994,6-Dichloro-5-(o-methoxyphenoxy)-2-methyl-pyrimidineHCID 131721323HCID 131721323, compound

Product 1

HCID 18184223HCID 18184223, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 1.0 g of 4,6-dichloro-5-(o-methoxyphenoxy)-2-methyl-pyrimidine in 20 ml of DMSO was added 1.76 g of 4-tert.-butyl-benzene sulfonamide potassium salt. The mixture was stirred for 72 h at room temperature. The solution was diluted with 250 ml of water and extracted twice with 200 ml of diehtyl ether. The organic layers were extracted twice with water. The combined aqueous layers were acidified to pH 4 with 5 ml of acetic acid and cooled to 0° C. The precipitated product was filtered off and dried in vacuo to give 1.05 g of 4-tert.-butyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-methyl-4-pyrimidinyl]-benzene sulfonamide as a pale beige powder. LC-MS: tR=5.64 min, [M+1]+=462.51, [M−1]−=460.63.

Workup

  1. extractionextracted twice with 200 ml of diehtyl ether
  2. extractionThe organic layers were extracted twice with water
  3. temperaturecooled to 0° C
  4. filtrationThe precipitated product was filtered off
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c067f942e3544ed5b777df1160b0b3a0
Source dataset
uspto-grants-2003_07
Patent number
US06596719B1

Reaction notes

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