Oxalyl chloride → (E)-4-(diMethylaMino)but-2-enoyl chloride

HRID 240568Notes

Reaction equation

HRID 240568 reaction equation
[ClH:1].[CH3:2][N:3]([CH3:10])[CH2:4]/[CH:5]=[CH:6]/[C:7](O)=[O:8].C(Cl)(=O)C([Cl:14])=O>C(#N)C.CN(C=O)C>[ClH:14].[CH3:2][N:3]([CH3:10])[CH2:4]/[CH:5]=[CH:6]/[C:7]([Cl:1])=[O:8]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochloride

Product 1

HCID 21917321(E)-4-(diMethylaMino)but-2-enoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To (E)-4-(dimethylamino)but-2-enoic acid hydrochloride (110 mg, 0.664 mmol) in acetonitrile (1.5 mL) was added oxalyl dichloride (75.9 mg, 0.598 mmol) followed by one drop of DMF. After heating to 60° C. for 30 minutes, the mixture was cooled to room temperature and concentrated to 0.5 mL total volume. The resulting solution was used without further purification.

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. concentrationconcentrated to 0.5 mL total volume
  3. customThe resulting solution was used without further purification

Sources & evidence

ORD record
ord-940ea291261347d392804a36dcf50bf6
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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