Potassium Carbonate → N-(1-isopropylpyrazol-5-yl)-5-(diethylaminosulfonyl) anthranilic acid

HRID 1586182Notes

Reaction equation

HRID 1586182 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[N:5]=[CH:4][CH:3]=1.Cl[C:11]1[CH:19]=[CH:18][C:17]([S:20]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])(=[O:22])=[O:21])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].CN(C=O)C>[CH:7]([N:6]1[C:2]([NH:1][C:11]2[C:12](=[CH:16][C:17]([S:20]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])(=[O:21])=[O:22])=[CH:18][CH:19]=2)[C:13]([OH:15])=[O:14])=[CH:3][CH:4]=[N:5]1)([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 7678952-Chloro-5-(diethylsulfamoyl)benzoic acidHCID 10903411-(propan-2-yl)-1H-pyrazol-5-amine

Product 1

HCID 54426707N-(1-isopropylpyrazol-5-yl)-5-(diethylaminosulfonyl) anthranilic acidYield 62.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-amino-1-isopropylpyrazole (6.43 g, 0.051 mol), 2-chloro-5-(diethylaminosulfonyl)benzoic acid (15.0 g, 0.051 mol), K2CO3 (7.04 g, 0.051 mol), Cu(OAc)2 (1.0 g) and DMF (100 ml) is refluxed for 24 hours. The reaction mixture is concentrated in vacuo, and the residue is poured into water and neutralized with acetic acid. The mixture is extracted with CH2Cl2 and the CH2Cl2 layer is dried over MgSO4 and evaporated to afford 12.1 g of N-(1-isopropylpyrazol-5-yl)-5-(diethylaminosulfonyl) anthranilic acid.

Workup

  1. temperatureis refluxed for 24 hours
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. additionthe residue is poured into water and neutralized with acetic acid
  4. extractionThe mixture is extracted with CH2Cl2
  5. dry with materialthe CH2Cl2 layer is dried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-efa105ccd8c74c919f1f7a9705b47f52
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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