Dichloromethane → 3-Phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutanimidate

HRID 1577660Notes

Reaction equation

HRID 1577660 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.[O:15]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.ClCCl>CCOCC.F[B-](F)(F)F.[Ag+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH:12]([CH3:14])[CH3:13])[C:9](=[NH:11])[O:10][CH2:25][C:24]2[CH:27]=[CH:28][CH:29]=[C:22]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:23]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 128981762-(4-Chlorophenyl)-3-methylbutanamide

Product 1

HCID 128981773-Phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutanimidate

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a refluxing solution of 2.72 g (12.9 mmol) of 2-(4-chlorophenyl)-3-methylbutyramide and 2.27 g (8.6 mmol) of 3-phenoxybenzyl bromide in a solution of 15 ml dichloromethane and 3 ml ethyl ether is added a solution of 1.83 g (9.5 mmol) of silver tetrafluoroborate in ether. The mixture is refluxed for 2 hours and then separated by pouring into ice cold aqueous ethyl acetate/sodium bicarbonate. The organic phase is washed with water, dried and stripped of solvent. The residue is triturated with ether and filtered. The filtrate is concentrated and chromatographed on silica gel, eluting with 25% ethyl acetate/hexane, and then on plates using 35% ethyl acetate/hexane, to yield 3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutanimidate, MS m/e 393 (M+).

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. customseparated
  3. additionby pouring into ice cold aqueous ethyl acetate/sodium bicarbonate
  4. washThe organic phase is washed with water
  5. customdried
  6. customThe residue is triturated with ether
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated
  9. customchromatographed on silica gel
  10. washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-eb24da71ec5142e4939e85c053b972e4
Source dataset
uspto-grants-1981_09
Patent number
US04288621

Reaction notes

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