Thionyl Chloride → HCID 21919298, compound

HRID 898691Notes

Reaction equation

HRID 898691 reaction equation
O=S(Cl)[Cl:3].[CH2:5]([O:7][C:8]1[CH:13]=[C:12]([O:14][CH2:15][CH3:16])[N:11]=[N:10][C:9]=1[CH2:17]O)[CH3:6]>C(Cl)Cl>[Cl:3][CH2:17][C:9]1[N:10]=[N:11][C:12]([O:14][CH2:15][CH3:16])=[CH:13][C:8]=1[O:7][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21919289HCID 21919289, compound

Product 1

HCID 21919298HCID 21919298, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Excess SOCl2 is added to a stirred solution of (4,6-diethoxy-pyridazin-3-yl)-methanol (174 mg, 0.88 mmol) in CH2Cl2 (4 mL). The reaction mixture is stirred at room temperature for 4 hours. The solvent is then removed in vacuo and toluene (4 mL) is added and evaporated to dryness. Flash column chromatography purification (eluted with 3:1 Hexane, EtOAc) of the residue provides the title product as a clear oil. H1 NMR δ (CDCl3) 6.28(s, 1H), 4.78 (s, 2H), 4.54 (q, 2H, J=7.2 Hz), 4.11 (q, 2H, J=7.2 Hz), 1.48 (t, 3H, J=7.2 Hz), 1.41 (t,3H, J=7.2 Hz,) LC-MS (M+1) 217.1.

Workup

  1. customThe solvent is then removed in vacuo and toluene (4 mL)
  2. additionis added
  3. customevaporated to dryness
  4. customFlash column chromatography purification (eluted with 3:1 Hexane, EtOAc) of the residue

Sources & evidence

ORD record
ord-979c9b55606b43a883b4fa69b9c68b46
Source dataset
uspto-grants-2008_04
Patent number
US07351826B2

Reaction notes

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