Thionyl Chloride → 4-[3-(Dibutylamino)propoxy]benzoyl chloride--hydrogen chloride (1/1)

HRID 971084Notes

Reaction equation

HRID 971084 reaction equation
[ClH:1].[CH2:2]([N:6]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH3:5].S(Cl)([Cl:26])=O>ClCCl>[ClH:26].[CH2:2]([N:6]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([Cl:1])=[O:16])=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 102690134-[3-(dibutylamino)propoxy]benzoic Acid Hydrochloride

Product 1

HCID 101092574-[3-(Dibutylamino)propoxy]benzoyl chloride--hydrogen chloride (1/1)Yield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(3-dibutylaminopropoxy)benzoic acid hydrochloride [19a] (3.44 g, 10.0 mmol), thionyl chloride (5.87 g, 3.6 mL, 49.4 mmol) and dichloromethane (10 mL) was stirred under reflux conditions for 1 hour and evaporated under reduced pressure at 60-70° C. (water bath) to give 3.62 g (100% yield) of 4-(3-dibutylaminopropoxy)benzoyl chloride hydrochloride [15].

Workup

  1. customevaporated under reduced pressure at 60-70° C. (water bath)

Sources & evidence

ORD record
ord-3b39f2eb57634b4d9e3ec02a809a4676
Source dataset
uspto-grants-2007_12
Patent number
US07312345B2

Reaction notes

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