Hydrochloric Acid → HCID 86753872, compound

HRID 1418329

Reaction equation

HRID 1418329 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][C:6]1[C:7]([Cl:14])=[N:8][C:9]([Cl:13])=[N:10][C:11]=1Cl.[C:19]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].[K].O.Cl>CS(C)=O>[C:19]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:32][C:11]2[C:6]([O:5][C:4]3[CH:15]=[CH:16][CH:17]=[CH:18][C:3]=3[O:2][CH3:1])=[C:7]([Cl:14])[N:8]=[C:9]([Cl:13])[N:10]=2)(=[O:30])=[O:31])=[CH:25][CH:24]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 53746905HCID 53746905, compoundHCID 66748434p-t-Butylbenzenesulfonamide potassium

Product 1

HCID 86753872HCID 86753872, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-(2-Methoxyphenoxy)-2,4,6-trichloropyrimidine (4) (4.8 g; 15.6 mmol) was dissolved in dimethyl sulfoxide (45 ml). Potassium 4-t-butylbenzenesulfonamide (8.0 g; 32 mmol) was added to the mixture while being cooled on ice, and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was poured into water, made acidic with hydrochloric acid, and extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and evaporated. The residue was recrystallized from ether, to thereby obtain 4.9 g (yield: 65%) of the title compound as colorless needles.

Workup

  1. temperaturewhile being cooled on ice
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-acd06b1c272d490387309d944c801387
Source dataset
uspto-grants-1999_03
Patent number
US05883092

Linked notes

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