Dimethylformamide → HCID 86680558, compound

HRID 334409Notes

Reaction equation

HRID 334409 reaction equation
S(Cl)(Cl)=O.C[N:6]([CH:8]=[O:9])C.[Cl:10][C:11]1[N:19]=[CH:18][C:17]([S:20](=[O:31])(=[O:30])[NH:21][C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[CH:23]=2)=[CH:16][C:12]=1C(O)=O.[OH-].[NH4+]>C1(C)C=CC=CC=1>[Cl:10][C:11]1[N:19]=[CH:18][C:17]([S:20](=[O:30])(=[O:31])[NH:21][C:22]2[CH:23]=[C:24]([F:29])[CH:25]=[C:26]([F:28])[CH:27]=2)=[CH:16][C:12]=1[C:8]([NH2:6])=[O:9]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 86680559HCID 86680559, compound

Product 1

HCID 86680558HCID 86680558, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

0.288 ml (3.87 mmol) of thionyl chloride and a drop of DMF are added successively to 0.450 g (1.29 mmol) of 2-chloro-5-(N-(3,5-difluorophenyl)sulfamoyl)nicotinic acid in 5 ml of anhydrous toluene. The mixture is placed under stirring, at reflux of toluene, for 2 hours. The acid chloride reaction mixture is then added drop by drop to an iced solution, under stirring, of 4.5 ml of 25% ammonium hydroxide. A release of gas is observed. The reaction medium is left under stirring at room temperature for 30 minutes. The reaction medium is extracted several times with ethyl acetate. The combined organic phases are dried on anhydrous sodium sulfate and then concentrated. 0.315 g of 2-chloro-5-(N-(3,5-difluorophenyl)sulfamoyl)nicotinamide in the form of a light brown solid is obtained (yield=72%).

Workup

  1. additionis then added drop by drop to an iced solution
  2. waitThe reaction medium is left
  3. stirringunder stirring at room temperature for 30 minutes
  4. extractionThe reaction medium is extracted several times with ethyl acetate
  5. dry with materialThe combined organic phases are dried on anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-865a7c64b83440afa87ecd3d824b874c
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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