Water → 4-tert.-butyl-N-[6-chloro-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamide

HRID 1358318Notes

Reaction equation

HRID 1358318 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.[K+].[C:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH-:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].O>CS(C)=O>[C:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:30][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:28])=[O:29])=[CH:23][CH:22]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 219795544,6-Dichloro-5-(4-methylphenyl)pyrimidineHCID 131721323HCID 131721323, compound

Product 1

HCID 227294154-tert.-butyl-N-[6-chloro-5-(p-tolyl)4-pyrimidinyl]-benzene sulfonamideYield 96.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 0.8 g of 4,6-dichloro-5-(p-tolyl)-pyrimidine and 1.68 g of 4-tert.-butylbenzene sulfonamide potassium salt in 20 ml of DMSO was stirred at room temperature for 24 h. The mixture was poured onto 200 ml of water and extracted twice with 100 ml of diethyl ether. The organic layers was extracted twice with 50 ml of water. The combined aqueous layers was acidified with conc. hydrochloric acid. The resulting fine suspension was extracted twice with ethyl acetate. The combined organic layers was dried over Na2SO4 and evaporated. The residue was dried under high vacuum to give 1.34 g 4-tert.-butyl-N-[6-chloro-5-(p-tolyl)-4-pyrimidinyl]-benzene sulfonamide as a white powder. LC-MS: tR=5.92 min, [M+1]+=416.20, [M−1]−=414.24.

Workup

  1. extractionextracted twice with 100 ml of diethyl ether
  2. extractionThe organic layers was extracted twice with 50 ml of water
  3. extractionThe resulting fine suspension was extracted twice with ethyl acetate
  4. dry with materialThe combined organic layers was dried over Na2SO4
  5. customevaporated
  6. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-494b30d6a5b24b96846952907ba0baac
Source dataset
uspto-grants-2003_07
Patent number
US06596719B1

Reaction notes

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