Methyl 2-chloroacrylate → HCID 11034029, compound

HRID 399258

Reaction equation

HRID 399258 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][N:4]=[C:5](Cl)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.Cl[C:17](=[CH2:22])[C:18]([O:20][CH3:21])=[O:19].N12CCCN=C1CCCCC2>CN(C)C=O>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([C:5]2[NH:4][C:3]([C:2]([F:15])([F:14])[F:1])=[CH:22][C:17]=2[C:18]([O:20][CH3:21])=[O:19])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6659Methyl 2-chloroacrylateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1180727188708-78-5

Product 1

HCID 11034029HCID 11034029, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(2,2,2-trifluoroethyl)-4-chlorobenzimidoyl chloride (10.2 g, 0.04 mol) and methyl 2-chloroacrylate (5.8 g, 0.048 mol) in N,N-dimethylformamide is treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 19.5 g, 0.128 mol) over 30 minutes at such a rate that the temperature is kept at 40° C., stirred for two hours, and quenched with water and ethyl acetate. The organic layer is separated, washed sequentially with aqueous HCl and water, and concentrated in vacuo to obtain an oil. Flash column chromatography of the oil using silica gel and a 20% ethyl acetate in heptane solution and crystallization from heptane gives the title product as white crystals (4.2 g, 34.6% yield, mp 120.0°-122.5° C.).

Workup

  1. customis kept at 40° C.
  2. customquenched with water and ethyl acetate
  3. customThe organic layer is separated
  4. washwashed sequentially with aqueous HCl and water
  5. concentrationconcentrated in vacuo
  6. customto obtain an oil
  7. customa 20% ethyl acetate in heptane solution and crystallization from heptane

Sources & evidence

ORD record
ord-813d463d2b574c59abd361db82714feb
Source dataset
uspto-grants-1998_10
Patent number
US05817834

Linked notes

Loading…