Chloromethyl methyl sulfide → 1-[(4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-3-[(methylsulfanyl)methyl]imidazolidin-4-one

HRID 63876

반응식

HRID 63876 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:32]([F:35])([F:34])[F:33])[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([N:25]4[CH2:29][C:28](=[O:30])[NH:27][CH2:26]4)=[O:24])=[C:19]([CH3:31])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[H-].[Na+].Cl[CH2:39][S:40][CH3:41]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:32]([F:33])([F:34])[F:35])[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([N:25]4[CH2:29][C:28](=[O:30])[N:27]([CH2:39][S:40][CH3:41])[CH2:26]4)=[O:24])=[C:19]([CH3:31])[CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

참가 물질

5

반응물 3

HCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 1180467971-[(4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]imidazolidin-4-one

생성물 1

HCID 1180466141-[(4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-3-[(methylsulfanyl)methyl]imidazolidin-4-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]imidazolidin-4-one (200 mg, 0.38 mmol, 1.00 equiv), tetrahydrofuran (10 mL), sodium hydride (30 mg, 0.75 mmol, 2.00 equiv, 60%), chloro(methylsulfanyl)methane (149 mg, 1.54 mmol, 4.00 equiv). The resulting solution was stirred for 1 h at 50° C. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 3×10 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×20 mL of brine. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel TLC-plate with ethyl acetate/petroleum ether (1/1). This resulted in 60 mg (27%) of 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-3-[(methylsulfanyl)methyl]imidazolidin-4-one as yellow oil.

후처리

  1. customInto a 100-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customThe reaction was then quenched by the addition of 10 mL of water
  4. extractionThe resulting solution was extracted with 3×10 mL of ethyl acetate
  5. washThe resulting mixture was washed with 3×20 mL of brine
  6. concentrationThe resulting mixture was concentrated under vacuum
  7. customThis resulted in 60 mg (27%) of 1-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-3-[(methylsulfanyl)methyl]imidazolidin-4-one as yellow oil

출처 및 근거

ORD 기록
ord-72a1b8389ce842f79206e09e3c8a7971
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447084B2

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