Thionyl Chloride → 4-(3-Diethylaminopropoxy)benzoyl chloride

HRID 346877Notes

Reaction equation

HRID 346877 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=1)[CH3:2].S(Cl)([Cl:21])=O>C(Cl)Cl>[CH2:1]([N:3]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([Cl:21])=[O:13])=[CH:10][CH:9]=1)[CH2:17][CH3:18])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 176070464-(3-(Diethylamino)propoxy)benzoic acid

Product 1

HCID 214352614-(3-Diethylaminopropoxy)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the compound from Example 2(ii)(6 g, 24 mmol) in DCM was stirred at 0° C. Thionyl chloride was added drop-wise and the reaction was heated at reflux for 24 hrs. The reaction was allowed to cool and the solvents removed under vacuum to afford the expected compound as a pungent crude solid. 5.9 g, 100%. The solid was used without further purification.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 24 hrs
  3. temperatureto cool
  4. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-8e2e87e7931545c7ac0028b3f0c20262
Source dataset
uspto-grants-2007_02
Patent number
US07173061B2

Reaction notes

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