Ethanol → N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-carboxybenzenesulfonamide

HRID 1155632Notes

Reaction equation

HRID 1155632 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][C:12]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]([O:26]C)=[O:25])(=[O:17])=[O:16])=[O:13])[N:4]=1.C(O)C.[OH-].[K+]>O.Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][C:12]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]([OH:26])=[O:25])(=[O:17])=[O:16])=[O:13])[N:4]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 10810737N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide

Product 1

HCID 13097297N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-carboxybenzenesulfonamideYield 100.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A mixture containing 5 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide, 20 ml of ethanol, 2.5 ml of water and 2.5 g of potassium hydroxide was stirred at ambient temperature and pressure for 18 hours. The mixture was then diluted with 250 ml of water and 20 ml of concentrated hydrochloric acid was added with stirring. The precipitate was filtered and washed with water and dried to yield 4.85 g of the desired product, melting at 161°-2° C. The infrared absorption peaks at 3500, 3400 and 1700 cm-1 are consistent with the desired structure and the nuclear magnetic resonance absorption peaks at 3.95 ppm, S, 6H, OCH3 of pyrimidine; 5.8 ppm S, 1H, pyrimidine proton at position 5; and 7.6-8.3 ppm, M, 4H, aromatic protons, are consistent with the desired structure.

Workup

  1. additionwas added
  2. stirringwith stirring
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-2620798b91114b5e8510726582e5ec4d
Source dataset
uspto-grants-1982_06
Patent number
US04332611

Reaction notes

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