Hydrochloric Acid → 4-(2-acetoxy-1,1-dimethylethyl)-N-{6-chloro-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide

HRID 1937413Notes

Reaction equation

HRID 1937413 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[C:6]([Cl:15])[N:5]=[CH:4][N:3]=1.[C:16]([O:19][CH2:20][C:21]([C:24]1[CH:29]=[CH:28][C:27]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1)([CH3:23])[CH3:22])(=[O:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+].Cl>C(OCC(C1C=CC(S(N)(=O)=O)=CC=1)(C)C)(=O)C.CS(C)=O>[C:16]([O:19][CH2:20][C:21]([C:24]1[CH:25]=[CH:26][C:27]([S:30]([NH:33][C:2]2[C:7]([C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=3)=[C:6]([Cl:15])[N:5]=[CH:4][N:3]=2)(=[O:31])=[O:32])=[CH:28][CH:29]=1)([CH3:23])[CH3:22])(=[O:18])[CH3:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 219795544,6-Dichloro-5-(4-methylphenyl)pyrimidineHCID 224610104-(2-Acetoxy-1,1-dimethylethyl)benzenesulfonamide

Product 1

HCID 224610114-(2-acetoxy-1,1-dimethylethyl)-N-{6-chloro-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamideYield 75.5%

Reagents, catalysts & solvents 2

HCID 224610104-(2-Acetoxy-1,1-dimethylethyl)benzenesulfonamideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4,6-dichloro-5-(4-methylphenyl)pyrimidine (10.0 g), 4-(2-acetoxy-1,1-dimethylethyl)benzenesulfonamide (11.58 g), potassium carbonate (14.45 g) and dimethyl-sulfoxide (50 ml) is stirred at 75° C. (bulk temperature) for 3 hours, and thereto is further added 4-(2-acetoxy-1,1-dimethylethyl)benzenesulfonamide (0.34 g). The mixture is stirred at 70-75° C. for 1.5 hour, and the reaction mixture is cooled, and poured into a mixture of ice (100 g) and conc. hydrochloric acid (60 ml). The mixture is extracted with ethyl acetate, and the organic layer is washed, dried, and concentrated under reduced pressure. The residue is crystallized from a mixture of ethyl acetate and diisopropyl ether to give 4-(2-acetoxy-1,1-dimethylethyl)-N-{6-chloro-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (14.97 g) as colorless needles.

Workup

  1. stirringThe mixture is stirred at 70-75° C. for 1.5 hour
  2. temperaturethe reaction mixture is cooled
  3. extractionThe mixture is extracted with ethyl acetate
  4. washthe organic layer is washed
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is crystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-0d105f583d0448929654425cb9de6ca0
Source dataset
uspto-grants-2002_05
Patent number
US06395741B1

Reaction notes

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