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

HRID 375900
Notes
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Reaction equation

HRID 375900 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8895
Cupric acetate
Catalyst
HCID 176Acetic AcidSolvent
HCID 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 ) was refluxed overnight. The reaction mixture was cooled to room temperature, poured into water and acidified with acetic acid to a pH of about 4-5. The mixture was extracted with CH2Cl2 and then the CH2Cl2 layer was evaporated to afford 4.5 g of N-(1-ethylpyrazol-5-yl)-5-(methylthio)anthranilic acid.

Workup

  1. temperaturewas refluxed overnight
  2. extractionThe mixture was extracted with CH2Cl2
  3. customthe CH2Cl2 layer was evaporated

Sources & evidence

ORD record
ord-1f4e05ed91ac4de19263bad4befd42fb
Source dataset
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05488055

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes