Thionyl Chloride → HCID 86729778, compound

HRID 2272620Notes

Reaction equation

HRID 2272620 reaction equation
[C:1]([OH:6])(=O)/[CH:2]=[CH:3]/[CH3:4].S(Cl)(Cl)=O.[NH2:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([Cl:20])[CH:13]=1>CC(N(C)C)=O.[Cl-].[Na+].O>[Cl:20][C:14]1[CH:13]=[C:12]([NH:11][C:1](=[O:6])/[CH:2]=[CH:3]/[CH3:4])[CH:19]=[CH:18][C:15]=1[C:16]#[N:17]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 887284-Amino-2-chlorobenzonitrileHCID 637090Crotonic Acid

Product 1

HCID 86729778HCID 86729778, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of crotonic acid (8.24 mL, 98.31 mmol) and thionyl chloride (7.18 mL, 98.31 mmol) in DMA (150 mL) was stirred at 0° C. for 1 hr. To the reaction mixture was added 4-amino-2-chlorobenzonitrile (15 g, 98.31 mmol), and the mixture was stirred at room temperature for additional 14 hr. To the reaction solution was added brine at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N aqueous sodium hydroxide solution and 1N hydrochloric acid, and dried, and the solvent was evaporated under reduced pressure to give (E)-N-(3-chloro-4-cyanophenyl)but-2-enamide (21.69 g, 98.31 mmol, quantitative) as a brownish-red powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1N aqueous sodium hydroxide solution and 1N hydrochloric acid
  3. customdried
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8fb54d31e29142a5b4f5d3d0a62c924a
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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