Dimethylformamide → HCID 21217699, compound

HRID 1586175Notes

Reaction equation

HRID 1586175 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) is heated at reflux overnight. The reaction mixture is poured into water, acidified with acetic acid and extracted with CH2Cl2. The CH2Cl2 layer is evaporated to afford N-(1-ethylpyrazol-5-yl)-5-(methylsulfonyl)anthranilic acid.

Workup

  1. temperatureis heated
  2. temperatureat reflux overnight
  3. extractionextracted with CH2Cl2
  4. customThe CH2Cl2 layer is evaporated

Sources & evidence

ORD record
ord-f3f6429c540c4cf1ab9e3dd2ae277565
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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