Chlorosuccinimide → 3-chloro-5-(diphenylmethyl)pyridin-2(1H)-one

HRID 2389373Notes

Reaction equation

HRID 2389373 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:21]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:21][C:10]1[C:11](=[O:14])[NH:12][CH:13]=[C:8]([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 227488105-(Diphenylmethyl)-2-pyridone

Product 1

HCID 685336193-chloro-5-(diphenylmethyl)pyridin-2(1H)-oneYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(diphenylmethyl)pyridin-2(1H)-one (0.3 g) and N-chlorosuccinimide(0.184 g) in DMF (3 mL) was stirred at ambient temperature for 23 hours. The reaction mixture was poured into saturated NaHCO3 aqueous solution and the resulting precipitates were collected by filtration and washed with water to afford 3-chloro-5-(diphenylmethyl)pyridin-2(1H)-one (0.31 g) as white powder.

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-6705fa2fea984a8f8b092e5008b27426
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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