Chlorosuccinimide → 6-Chlorooxazolo[4,5-b]pyridin-2(3H)-one

HRID 1710644Notes

Reaction equation

HRID 1710644 reaction equation
[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]1=[O:10].C1C(=O)N([Cl:18])C(=O)C1>C(#N)C.C(OCC)(=O)C>[Cl:18][C:7]1[CH:8]=[C:9]2[O:1][C:2](=[O:10])[NH:3][C:4]2=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 2799900Oxazolo(4,5-b)pyridin-2(3H)-one

Product 1

HCID 136144596-Chlorooxazolo[4,5-b]pyridin-2(3H)-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3H-oxazolo[4,5-b]pyridin-2-one (36) (300 mg, 2.2 mmol, 1 equiv) and NCS (352 mg, 2.65 mmol, 1.2 equiv) in 5 mL of acetonitrile was heated at 85° C. overnight. The reaction solution was diluted with ethyl acetate (EtOAc), and washed with water. The organic solution was concentrated and purified by flash chromatography, to provide 6-Chloro-3H-oxazolo[4,5-b]pyridin-2-one (37): LCMS Retention time, 0.69 min; LCMS observed (M+H)+: 171.

Workup

  1. washwashed with water
  2. concentrationThe organic solution was concentrated
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-b685e7efec2b47bdb2a09c8e91b76985
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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