Chloromethyl Methyl Ether → N-(1-(4-chloromethylphenyl)cyclopropyl)acetamide

HRID 1282127Notes

Reaction equation

HRID 1282127 reaction equation
[C:1]1([C:7]2([NH:10][C:11](=[O:13])[CH3:12])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[CH2:16][Cl:17]>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[Cl:17][CH2:16][C:4]1[CH:5]=[CH:6][C:1]([C:7]2([NH:10][C:11](=[O:13])[CH3:12])[CH2:8][CH2:9]2)=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 7864Chloromethyl Methyl EtherHCID 18423125HCID 18423125, compound

Product 1

HCID 18423039N-(1-(4-chloromethylphenyl)cyclopropyl)acetamide

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(1-phenylcyclopropyl)acetamide (5.0 g) in methylene chloride (35 ml) was added titanium tetrachloride (6.26 ml) under ice-cooling and to this solution was added dropwise a solution of methoxymethyl chloride (4.33 ml) in methylene chloride (15 ml) over 10 min under ice-cooling. The mixture was stirred at room temperature for 14 hr. The reaction mixture was poured into ice water and extracted with chloroform (50 ml). The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate) to give the title compound (3.71 g) as white crystals, m.p.=124-127° C.

Workup

  1. temperaturecooling and to this solution
  2. temperaturecooling
  3. extractionextracted with chloroform (50 ml)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe obtained residue was purified by silica gel column chromatography (developing solvent; ethyl acetate)

Sources & evidence

ORD record
ord-60ba80e106a94bdbba6f1af1a597fe2e
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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