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

HRID 899388Notes

Reaction equation

HRID 899388 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 h. 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 over (Na2SO4). The mixture was concentrated in vacuo to give 0.74 g of a 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 over (Na2SO4)
  5. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-f7b5b9ef9a334a48824fbad0b799446b
Source dataset
uspto-grants-2008_04
Patent number
US07354941B2

Reaction notes

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