Triethylamine → Ethyl (2Z)-2-((2,6-dichloropyridin-3-yl)carbonyl)-3-(dimethylamino)prop-2-enoate

HRID 1696934Notes

Reaction equation

HRID 1696934 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].CN[C:14]([NH:21][CH3:22])=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[CH2:23](N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([C:4](/[C:15](=[CH:14]/[N:21]([CH3:22])[CH3:23])/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:5])=[CH:7][CH:8]=[C:9]([Cl:11])[N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122639842,6-Dichlorpyridine-3-carbonyl chlorideHCID 85819813Ethyl 3,3-dimethylaminoacrylate

Product 1

HCID 15675736Ethyl (2Z)-2-((2,6-dichloropyridin-3-yl)carbonyl)-3-(dimethylamino)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,6-dichloronicotinoyl chloride (62.5 g), ethyl 3,3-dimethylaminoacrylate (58.8 g) and triethylamine (69 g) in toluene (600 mL) was stirred at 90° C. for 1 hour then cooled and concentrated. The concentrate was dissolved in dichloromethane (60 mL), diluted with diethyl ether, and filtered. The filtrate was concentrated, and the concentrate was crystallized from dichloromethane/diethyl ether/hexanes.

Workup

  1. temperaturethen cooled
  2. concentrationconcentrated
  3. dissolutionThe concentrate was dissolved in dichloromethane (60 mL)
  4. additiondiluted with diethyl ether
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe concentrate was crystallized from dichloromethane/diethyl ether/hexanes

Sources & evidence

ORD record
ord-59468fef94ac434f8f11f2f60a94b9e2
Source dataset
uspto-grants-2012_04
Patent number
US08163769B2

Reaction notes

Loading…