Thionyl Chloride → 4-[(3,5-dimethylphenyl)-thio]-5-(chloromethyl)-6-methyl-2(1H)-pyridinone

HRID 1241537Notes

Reaction equation

HRID 1241537 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[C:15]([CH2:16]O)=[C:14]([CH3:18])[NH:13][C:12](=[O:19])[CH:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.O=S(Cl)[Cl:22]>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[C:15]([CH2:16][Cl:22])=[C:14]([CH3:18])[NH:13][C:12](=[O:19])[CH:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 219352934-[(3,5-dimethylphenyl)-thio]-5-(hydroxymethyl)-6-methyl-2(1H)-pyridinone

Product 1

HCID 219353114-[(3,5-dimethylphenyl)-thio]-5-(chloromethyl)-6-methyl-2(1H)-pyridinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of intermediate 15 (275 mg; 1 mmol) in dichloromethane (10 ml) became homogeneous by addition of SOCl2 (2.3 ml) at room temperature. After 2 hours of stirring at room temperature, all the volatiles were removed under reduced pressure giving a yellow solid which corresponds to the expected intermediate 16 in quantitative yield (294 mg).

Workup

  1. customall the volatiles were removed under reduced pressure
  2. customgiving a yellow solid which

Sources & evidence

ORD record
ord-06a659da66df4a499cb64409958e929e
Source dataset
uspto-grants-2006_10
Patent number
US07115608B2

Reaction notes

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