Dimethylformamide dimethyl acetal → Ethyl 2-[2,4-dichloro-5-(2-chloro-4,6-difluorophenylamino)benzoyl]-3-dimethylaminoacrylate

HRID 749487Notes

Reaction equation

HRID 749487 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([NH:9][C:10]2[C:15]([F:16])=[CH:14][C:13]([F:17])=[CH:12][C:11]=2[Cl:18])=[CH:4][C:3]=1[C:19](=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].CO[CH:29](OC)[N:30]([CH3:32])[CH3:31]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([NH:9][C:10]2[C:15]([F:16])=[CH:14][C:13]([F:17])=[CH:12][C:11]=2[Cl:18])=[CH:4][C:3]=1[C:19]([C:20](=[CH:29][N:30]([CH3:32])[CH3:31])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:26]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 68799347Ethyl 3-[2,4-dichloro-5-(2-chloro-4,6-difluorophenylamino)phenyl]-3-oxopropionate

Product 1

HCID 68796206Ethyl 2-[2,4-dichloro-5-(2-chloro-4,6-difluorophenylamino)benzoyl]-3-dimethylaminoacrylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3.88 g (crude) of ethyl 3-[2,4-dichloro-5-(2-chloro-4,6-difluorophenylamino)phenyl]-3-oxopropionate and 1.22 g (0.10 mmol) of dimethylformamide dimethyl acetal in 10 ml of toluene were heated to reflux for 1.5 hours. The mixture was cooled to room temperature and concentrated in vacuo. Purification on silica gel (petroleum ether) (45-70° C.)/ethyl acetate, 8 minutes isocratic 35% ethyl acetate, then to 60% ethyl acetate in 7 minutes, flow rate 400 ml/minute) afforded 3.59 g (82% over the two stages) of the desired product.

Workup

  1. temperatureto reflux for 1.5 hours
  2. concentrationconcentrated in vacuo
  3. customPurification on silica gel (petroleum ether) (45-70° C.)/ethyl acetate, 8 minutes isocratic 35% ethyl acetate

Sources & evidence

ORD record
ord-6d80251b025d41e1a14452d4e43415c4
Source dataset
uspto-grants-2008_07
Patent number
US07402674B2

Reaction notes

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