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

HRID 375898Notes

Reaction equation

HRID 375898 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) was refluxed for 24 hours. The reaction mixture was concentrated in vacuo and the residue was poured into water and neutralized with acetic acid. The mixture was extracted with CH2Cl2 and the CH2Cl2 layer was dried over MgSO4 and evaporated to afford 12.1 g of N-(1-isopropylpyrazol-5-yl)-5-(diethylaminosulfonyl) anthranilic acid.

Workup

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

Sources & evidence

ORD record
ord-7a29c6d369524198a1e96d492f38183b
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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