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

HRID 126976

반응식

HRID 126976 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 159722Silver tetrafluoroborate촉매HCID 3283Diethyl Ether용매2회

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-2e3a9f3858cd4cdd9377665e6ee2c8c1
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04254264

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