Water → HCID 67308893, compound

HRID 2383338Notes

Reaction equation

HRID 2383338 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). The precipitated solid was collected by filtration, and washed with water and hexane to give 5-(4-bromonaphthalene-2-yl)-[1,3,4]oxathiazole-2-one (1.13 g). This compound (1.12 g) was dissolved in dichlorobenzene (18 mL). To the solution was added ethyl cyanoformate (1.42 mL), and the mixture was stirred at 160° C. for 22 hours. To the mixture was added water (30 mL) at room temperature, and the resulting mixture was extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate) to give the title compound (1.21 g).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water and hexane

Sources & evidence

ORD record
ord-42f8fea5db37440386675d75cbbb4fb6
Source dataset
uspto-grants-2012_09
Patent number
US08263622B2

Reaction notes

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