Sodium Hydroxide → HCID 12832225, compound

HRID 1447065Notes

Reaction equation

HRID 1447065 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:9][C:10](=[O:17])[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][CH:7]=1.C(=O)(O)[O-].[Na+].[CH3:23][S:24](Cl)(=[O:26])=[O:25].[OH-].[Na+]>C(#N)C.O>[CH3:23][S:24]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:9][C:10](=[O:17])[C:11](=[CH:15][CH:16]=2)[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][CH:7]=1)(=[O:26])=[O:25]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 12832224HCID 12832224, compound

Product 1

HCID 12832225HCID 12832225, compoundYield 29.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A suspension of 1.15 g (5 mmol) of 6-(3-aminophenyl)-1,2-dihydro-2-oxonicotinic acid, 200 ml of water, and 0.42 g (5 mmol) of sodium bicarbonate is stirred at 0°-5° and a solution of 3.6 ml (30 mmol) of methanesulfonyl chloride and 30 ml of acetonitrile is added over a 2 hr. period. During the addition, the pH of the reaction is maintained at 6.9-7.3 with 1 N sodium hydroxide. After the addition, the reaction is stirred at 0°-5° for 2 hrs. The precipitated solid is filtered and dried to give 0.45 g of 6-[3-(methylsulfonylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid.

Workup

  1. additionDuring the addition
  2. additionAfter the addition
  3. stirringthe reaction is stirred at 0°-5° for 2 hrs
  4. filtrationThe precipitated solid is filtered
  5. customdried

Sources & evidence

ORD record
ord-4db97204365f4ef0ba321d50fff0cb4f
Source dataset
uspto-grants-1982_02
Patent number
US04315014

Reaction notes

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