Thionyl Chloride → 6-Chloro-3-chloromethyl-4-methoxypyridazine

HRID 1244249Notes

Reaction equation

HRID 1244249 reaction equation
O=S(Cl)[Cl:3].[Cl:5][C:6]1[N:11]=[N:10][C:9]([CH2:12]O)=[C:8]([O:14][CH3:15])[CH:7]=1>C(Cl)Cl>[Cl:5][C:6]1[N:11]=[N:10][C:9]([CH2:12][Cl:3])=[C:8]([O:14][CH3:15])[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21919279(6-Chloro-4-methoxypyridazin-3-YL)methanol

Product 1

HCID 219192946-Chloro-3-chloromethyl-4-methoxypyridazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Excess SOCl2 is added to a stirred solution of (6-chloro-4-methoxy-pyridazin-3-yl)-methanol (140 mg, 0.8 mmol) in CH2Cl2 (4 mL). The reaction mixture is stirred at room temperature for 4 hours. The solvent is removed in vacuo; toluene (4 mL) is added and evaporated to dryness. Flash column chromatography (silica gel) purification of the residue provides 6-chloro-3-chloromethyl-4-methoxy-pyridazine as a clear oil.

Workup

  1. customThe solvent is removed in vacuo
  2. additiontoluene (4 mL) is added
  3. customevaporated to dryness
  4. customFlash column chromatography (silica gel) purification of the residue

Sources & evidence

ORD record
ord-7dc2075a0418446cb3fd2714965154c1
Source dataset
uspto-grants-2006_10
Patent number
US07122546B2

Reaction notes

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