Water → HCID 67308893, compound

HRID 2383339Notes

Reaction equation

HRID 2383339 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]([NH2:14])=[O:13])[CH:3]=1.Cl[C:16]([S:18]Cl)=[O:17].O>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([C:12]2[O:13][C:16](=[O:17])[S:18][N:14]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 75990(Chlorothio)formyl chlorideHCID 540847794-Bromo-2-naphthalenecarboxamide

Product 1

HCID 67308893HCID 67308893, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-bromonaphthalene-2-carboxylic amide (1.10 g) in toluene (11.0 mL) was added chlorocarbonylsulfenyl chloride (0.73 mL), and the mixture was stirred at 100° C. for 18 hours. To the reaction solution was added water (50 mL), and the precipitated solid was collected by filtration. The obtained solid was washed with water and hexane to give 5-(4-bromonaphthalene-2-yl)-[1,3,4]oxathiazole-2-one (1.13 g). This compound (1.13 g) was dissolved in dichlorobenzene (18 mL). To the solution was added ethyl propiolate (1.52 mL), and the mixture was stirred at 160° C. for 18 hours. The reaction solution was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate) to give the title compound (0.66 g).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washThe obtained solid was washed with water and hexane

Sources & evidence

ORD record
ord-8f8fb22f20bf47fd95b5a0a918290eea
Source dataset
uspto-grants-2012_09
Patent number
US08263622B2

Reaction notes

Loading…