Pyridine → HCID 86591959, compound

HRID 416545Notes

Reaction equation

HRID 416545 reaction equation
[CH2:1](N/[C:9](/[CH3:17])=[C:10](/[CH3:16])\[C:11]([O:13]CC)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:18]1C=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH3:24][O:25]CC(Cl)=O.C([O:32]CC)C>>[CH2:21]([CH2:20][C:19]([NH:18][O:25][CH2:24][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:32])[CH3:22].[CH3:16]/[C:10](=[CH:9]\[CH3:17])/[C:11]([O-:13])=[O:12]

Participants

5

Reactant 4

HCID 1049PyridineHCID 3283Diethyl Ether2×HCID 96623Methoxyacetyl chlorideHCID 15716741HCID 15716741, compound

Product 1

HCID 86591959HCID 86591959, compoundYield 91.3%

Procedure

Ethyl 3-benzylamino-2-methylcrotonate (1-004-02) (97.83 g) was dissolved in diethyl ether (2 L). The reaction mixture was stirred under ice-cooling and nitrogen atmosphere. After pyridine (35.6 mL) was added to the reaction mixture, a solution of methoxyacetyl chloride (40.2 mL) in diethyl ether was added dropwise to the reaction mixture at 5 to 6° C. as internal temperature for 45 min. After 2 h, the reaction mixture was poured into ice-water (1.5 L), extracted twice with diethyl ether, and washed with water (1 L) and an aqueous solution of sodium bicarbonate. The extract was dried over magnesium sulfate, and evaporated under reduced pressure to give ethyl 1-benzylmethoxyacetamide-2-methylcrotonate (1-004-03) (111.47 g, 91.3%) as an oil.

Workup

  1. temperaturecooling
  2. extractionextracted twice with diethyl ether
  3. washwashed with water (1 L)
  4. dry with materialThe extract was dried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a22c546533c3491cac08fc42eb56418a
Source dataset
uspto-grants-2012_01
Patent number
US08088924B2

Reaction notes

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