Dimethylformamide → HCID 21217699, compound

HRID 375891Notes

Reaction equation

HRID 375891 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:15][C:16]1[N:20]([CH2:21][CH3:22])[N:19]=[CH:18][CH:17]=1.CN(C=O)C.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Cu+2].C(O)(=O)C.O>[CH2:21]([N:20]1[C:16]([NH:15][C:2]2[C:3](=[CH:7][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:17][CH:18]=[N:19]1)[CH3:22]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 3373101-Ethyl-1H-pyrazol-5-amineHCID 23291322-Chloro-5-(methylsulphonyl)benzoic acid

Product 1

HCID 21217699HCID 21217699, compound

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 2-chloro-5-(methylsulfonyl)benzoic acid (5.0 g, 21.4 mmol), 5-amino-1-ethylpyrazole (2.4 g, 21.4 mmol), DMF (50 ml), Cu(OAc)2 (0.5 g) and K2CO3 (2.76 g, 20 mmol) was heated at reflux overnight. The reaction mixture was poured into water, acidified with acetic acid and extracted with CH2Cl2. The CH2Cl2 layer was evaporated to afford N-(1-ethylpyrazol-5-yl)-5-(methylsulfonyl)anthranilic acid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionextracted with CH2Cl2
  4. customThe CH2Cl2 layer was evaporated

Sources & evidence

ORD record
ord-7b5a7d03ef7d48c1824a9951a9acc4ec
Source dataset
uspto-grants-1996_01
Patent number
US05488055

Reaction notes

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