Thionyl Chloride → N-(6-chloromethyl-pyridin-2-yl)-2,2-dimethyl-propionamide

HRID 1454859Notes

Reaction equation

HRID 1454859 reaction equation
O[CH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[CH:5][CH:4]=1.S(Cl)([Cl:18])=O>C(Cl)Cl>[Cl:18][CH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21782926N-[6-(Hydroxymethyl)pyridin-2-yl]-2,2-dimethylpropanamide

Product 1

HCID 68845579N-(6-chloromethyl-pyridin-2-yl)-2,2-dimethyl-propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(6-Hydroxymethyl-pyridin-2-yl)-2,2-dimethyl-propionamide (2.03 g) in CH2Cl2 (75 mL) was treated at RT with thionyl chloride (1.785 mL) and then heated to reflux for 1.5 h. The reaction mixture was cooled to RT and partitioned between water and AcOEt, the layers were separated, the organic layer dried over MgSO4, filtered and evaporated to give N-(6-chloromethyl-pyridin-2-yl)-2,2-dimethyl-propionamide (0.66 g) as a brown liquid. MS (ESI): 227.2 (MH+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 h
  3. custompartitioned between water and AcOEt
  4. customthe layers were separated
  5. dry with materialthe organic layer dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-cf5706fe3a1c4897962168d70fed2d36
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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