Dichloromethane → N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide

HRID 1789291Notes

Reaction equation

HRID 1789291 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.C(Cl)Cl.[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([N:28]=[C:29]=[O:30])(=[O:27])=[O:26])=[O:18].[OH-].[Na+]>O>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([NH:1][C:29]([NH:28][S:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:17]([O:16][CH3:15])=[O:18])(=[O:27])=[O:26])=[O:30])[N:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester

Product 1

HCID 10810737N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamideYield 43.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture containing 1.6 g of 2-amino-4,6-dimethoxypyrimidine, 30 ml of anhydrous methylene chloride and 2.4 g of 2-methoxycarbonylbenzenesulfonylisocyanate was stirred at ambient temperature and pressure for 16 hours. It was then filtered to remove unreacted amine and the filtrate evaporated at temperatures up to 40° and reduced pressure. The residue thus obtained was stirred in 25 ml of water, the pH adjusted to 10 by the addition of 50% aqueous sodium hydroxide and the solution filtered. Acidification of the filtrate to pH 3 caused the formation of a precipitate. Filtration and drying the precipitate yielded 1.7 g of the desired product, melting at 185°-190°. Its infrared absorption peaks at 1700 and 1710 cm-1 are consistent for the desired structure and the nuclear magnetic resonance absorption peaks at 3.8 and 3.85 are consistent for the two different types of methoxy groups brought together in this product.

Workup

  1. filtrationIt was then filtered
  2. customto remove unreacted amine
  3. customthe filtrate evaporated at temperatures up to 40°
  4. customThe residue thus obtained
  5. filtrationthe solution filtered
  6. filtrationFiltration
  7. customdrying the precipitate

Sources & evidence

ORD record
ord-61626fc7d5534f01883eebf809b6b0d7
Source dataset
uspto-grants-1987_08
Patent number
US04689072

Reaction notes

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