Methyl Isocyanate → 1-[Cyclopentyloxy-(3,4-dichloro-phenyl)-acetyl]-3-methyl-urea

HRID 397206ノート

反応式

HRID 397206 の反応式
[CH:1]1([O:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([NH2:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][N:20]=[C:21]=[O:22]>C1(C)C=CC=CC=1>[CH:1]1([O:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([NH:10][C:21]([NH:20][CH3:19])=[O:22])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 2

HCID 12228Methyl IsocyanateHCID 18172596Rac-2-cyclopentyloxy-2-(3,4-dichloro-phenyl)-acetamide

生成物 1

HCID 99281201-[Cyclopentyloxy-(3,4-dichloro-phenyl)-acetyl]-3-methyl-urea収率 41%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of rac-2-cyclopentyloxy-2-(3,4-dichloro-phenyl)-acetamide (116 mg, 0.40 mmol) in toluene (5 mL) was treated with methyl isocyanate (0.04 mL, 0.60 mmol). The resulting solution was heated to reflux for 24 h, then was cooled and was evaporated under reduced pressure. The resulting oil was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 60/40 hexanes/ethyl acetate) to furnish 1-[cyclopentyloxy-(3,4-dichloro-phenyl)-acetyl]-3-methyl-urea (30 mg, 41% yield) as a colorless oil: EI-HRMS m/e calcd for C15H18N2Cl2O3 (M+) 288.0558, found 288.0572.

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 24 h
  3. temperaturewas cooled
  4. customwas evaporated under reduced pressure
  5. customThe resulting oil was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 60/40 hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-5d38fa0190b54316a74b77d3c0987dd4
出典データセット
uspto-grants-2003_08
特許番号
US06608218B2

反応ノート

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