Water → 2-(Benzo[2,1,3]thiadiazol-5-yloxy)-nicotinic acid ethyl ester

HRID 350970Notes

Reaction equation

HRID 350970 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1Cl)[CH3:2].[N:13]1[S:14][N:15]=[C:16]2[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:17]=12.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[O:22][C:20]1[CH:19]=[CH:18][C:17]2=[N:13][S:14][N:15]=[C:16]2[CH:21]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27718862,1,3-Benzothiadiazol-5-olHCID 2796614Ethyl chloronicotinate

Product 1

HCID 235293462-(Benzo[2,1,3]thiadiazol-5-yloxy)-nicotinic acid ethyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-chloro-nicotinic acid ethyl ester (0.516 g, 3 mmol), benzo-[2,1,3]-thiadiazol-5-ol (0.46 g, 3 mmol) and cesium carbonate (2.07 g, 6.3 mmol) was stirred in 40 mL N,N-dimethylformamide at 80° C. for 48 hours. The dark orange mixture was cooled and poured into water (600 mL) and extracted with ethyl acetate. The combined organic layers were washed with water and brine, and dried (Na2SO4). The mixture was concentrated in vacuo to give 0.74 g yellow solid (82% yield).

Workup

  1. temperatureThe dark orange mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-1d650088cab04d398cb460254b95b7db
Source dataset
uspto-grants-2007_02
Patent number
US07183293B2

Reaction notes

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