3,4-Dimethoxybenzenesulfonyl chloride → 3,4-Dimethoxy-N-[5-(4-methoxyphenyl)-pyrimidine-2-yl]benzenesulfonamide

HRID 1258615Notes

Reaction equation

HRID 1258615 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][C:12]([NH2:15])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([S:26](Cl)(=[O:28])=[O:27])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25]>N1C=CC=CC=1>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([S:26]([NH:15][C:12]2[N:11]=[CH:10][C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)=[CH:14][N:13]=2)(=[O:27])=[O:28])[CH:21]=[CH:22][C:23]=1[O:24][CH3:25]

Participants

4

Reactant 2

HCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 445585905-(4-Methoxyphenyl)pyrimidin-2-amine

Product 1

HCID 249948133,4-Dimethoxy-N-[5-(4-methoxyphenyl)-pyrimidine-2-yl]benzenesulfonamideYield 33.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-(4-methoxyphenyl)pyrimidin-2-amine (302 mg, 1.5 mmol) in 10 mL of dry pyridine was added 3,4-dimethoxybenzenesulfonyl chloride (398 mg, 1.68 mmol). The solution was stirred at room temperature under Argon. After 24 h, the pyridine was removed in vacuo and flashed off with toluene. The residue was partitioned between EtOAc and 1M HCl. EtOAc phase was washed with water to neutral, dried over Na2SO4 and evaporated in vacuo to give 0.20 g of a solid which was taken up in 4 mL of hot HOAc, diluted with 2 mL of water which initiated crystallization to give 181 mg of product with mp 218-220° C.

Workup

  1. customthe pyridine was removed in vacuo
  2. customThe residue was partitioned between EtOAc and 1M HCl
  3. washEtOAc phase was washed with water to neutral,
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-a8011eee08014c5cb6c5c7cff2199e98
Source dataset
uspto-grants-2013_06
Patent number
US08466182B2

Reaction notes

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