Thionyl Chloride → HCID 88897500, compound

HRID 1914913Notes

Reaction equation

HRID 1914913 reaction equation
[C:1](/[C:3](/[CH:13]=[CH2:14])=[CH:4]\[C@@H:5]1[C@@H:7]([C:8](O)=[O:9])[C:6]1([CH3:12])[CH3:11])#[N:2].S(Cl)([Cl:17])=O>O1CCCC1.CN(C)C=O>[C:1](/[C:3](/[CH:13]=[CH2:14])=[CH:4]\[C@@H:5]1[C@@H:7]([C:8]([Cl:17])=[O:9])[C:6]1([CH3:12])[CH3:11])#[N:2]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 86675791HCID 86675791, compound

Product 1

HCID 88897500HCID 88897500, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

(1R)-trans-3-[(1Z)-2-cyano-1,3-butadienyl]-2,2-dimethylcyclopropanecarboxylic acid (440 mg, 2.30 mmol) was dissolved in 3 mL of tetrahydrofuran and then thionyl chloride (301 mg, 2.53 mmol) and 10 mg of N,N-dimethylformamide were added and the solution was stirred at room temperature for 1 hours, and further at 60° C. of 3 hours. The reaction solution was concentrated under reduced pressure condition to obtain 460 mg of (1R)-trans-3-[(1Z)-2-cyano-1,3-butadienyl]-2,2-dimethylcyclopropanecarboxylic acid chloride represented by the following formula:

Workup

  1. waitfurther at 60° C. of 3 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure condition

Sources & evidence

ORD record
ord-ff8f602ed0df47f4b0f38206f1ff87d5
Source dataset
uspto-grants-2013_12
Patent number
US08614241B2

Reaction notes

Loading…