Dimethylformamide → 1-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride

HRID 869898Notes

Reaction equation

HRID 869898 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([OH:15])=O)[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.S(Cl)([Cl:18])=O.CN(C)C=O>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([Cl:18])=[O:15])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 143496081-(1,3-Dioxaindan-5-yl)cyclopropane-1-carboxylic acid

Product 1

HCID 591291541-(Benzo[d][1,3]dioxol-5-yl)cyclopropanecarbonyl chloride

Procedure

To 1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxylic acid (100 mg, 0.50 mmol) in thionyl chloride (110 μL, 1.5 mmol) was added N,N-dimethylformamide (20 μL, 0.26 mmol). The reaction mixture was stirred at room temperature for 30 minutes. Excess thionyl chloride and N,N-dimethylformamide were removed in vacuo and the resulting acid chloride was used directly in next step.

Workup

  1. customExcess thionyl chloride and N,N-dimethylformamide were removed in vacuo

Sources & evidence

ORD record
ord-043a6f788db945088b56a31b204e941c
Source dataset
uspto-grants-2015_03
Patent number
US08969386B2

Reaction notes

Loading…