Water → HCID 45117061, compound

HRID 2111003Notes

Reaction equation

HRID 2111003 reaction equation
[CH:1]1[C:6]([CH2:7][Cl:8])=[CH:5][CH:4]=[C:3](/[C:9](/Cl)=[N:10]\[OH:11])[CH:2]=1.CO[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[O:18].C(N(CC)CC)C.O>ClCCl>[Cl:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([C:9]2[C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][O:11][N:10]=2)=[CH:2][CH:1]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2724617Methyl 3-methoxyprop-2-enoateHCID 91622765HCID 91622765, compound

Product 1

HCID 45117061HCID 45117061, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Hydroxy-4-chloromethylbenzenecarboxyimidoyl chloride (15.27 g, 74.82 mmol) was dissolved in dichloromethane (300 ml), methyl 3-methoxyacrylate (10.43 g, 89.82 mmol) was added, and triethylamine (21 ml, 151 mmol) was slowly added dropwise. The mixture was stirred overnight at room temperature. Water was added, and the mixture was extracted with dichloromethane. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=5:1) to give the title compound (9.67 g, 51%).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained crude product
  6. customwas purified by silica gel chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-a3a1861b58df4dc7b771d683206694cb
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

Loading…