Dimethylformamide → N-(1-ethylpyrazol-5-yl)-5-(methylthio)anthranilic acid

HRID 1586184Notes

Reaction equation

HRID 1586184 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CN(C=O)C.[NH2:18][C:19]1[N:23]([CH2:24][CH3:25])[N:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C.O>[CH2:24]([N:23]1[C:19]([NH:18][C:2]2[C:3](=[CH:7][C:8]([S:11][CH3:12])=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:20][CH:21]=[N:22]1)[CH3:25]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3373101-Ethyl-1H-pyrazol-5-amineHCID 6088142-Chloro-5-(methylsulfanyl)benzoic acid

Product 1

HCID 21217703N-(1-ethylpyrazol-5-yl)-5-(methylthio)anthranilic acidYield 37.7%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 2-chloro-5-(methylthio)benzoic acid (8.8 g, 0.043 mol), DMF (100 ml), 5-amino-1-ethylpyrazole (4.8 g, 0.043 mol), K2CO3 (5.94 g, 0.043 mol) and Cu(OAc)2 (0.5 g ) is refluxed overnight. The reaction mixture is cooled to room temperature, poured into water and acidified with acetic acid to a pH of about 4-5. The mixture is extracted with CH2Cl2 and then the CH2Cl2 layer is evaporated to afford 4.5 g of N-(1-ethylpyrazol-5-yl)-5-(methylthio)anthranilic acid.

Workup

  1. temperatureis refluxed overnight
  2. extractionThe mixture is extracted with CH2Cl2
  3. customthe CH2Cl2 layer is evaporated

Sources & evidence

ORD record
ord-348c2d7f5c75414990811303d9a2ecaf
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

Loading…