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

反応式

HRID 63876 の反応式
[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

参加物

5

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-72a1b8389ce842f79206e09e3c8a7971
出典データセット
uspto-grants-2016_09
特許番号
US09447084B2

関連ノート

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