Hydrochloric Acid → 1-[(3-Acetylphenyl)methyl]-3-(4-chlorophenyl)urea

HRID 64230ノート

反応式

HRID 64230 の反応式
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3([CH3:25])OCC[O:21]3)[CH:15]=2)=[O:11])=[CH:5][CH:4]=1>C1COCC1>[C:20]([C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][NH:12][C:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=1)=[O:11])(=[O:21])[CH3:25]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 715005361-(4-Chlorophenyl)-3-(3-(2-methyl-1,3-dioxolan-2-yl)benzyl)urea

生成物 1

HCID 469169831-[(3-Acetylphenyl)methyl]-3-(4-chlorophenyl)urea収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A 2N HCl solution was added to a solution of 22 (165 mg, 0.479 mmol) in THF (2 mL). The mixture was refluxed for several hours until the starting materials were consumed. The reaction mixture was allowed to cool to room temperature, quenched with solid NaHCO3, and then the volatiles were removed under reduced pressure. The residue was diluted with ethyl acetate and then washed with water. The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by chromatography to give 23 (144 mg, 100%) 1H NMR (DMSO-d, 400 MHz) δ 4.44 (d, J=5.6 Hz, 2H), 5.37 (t, J=3.7 Hz, 1H), 6.83 (s, 1H), 7.20-7.26 (5H, m), 7.40 (t, J=7.6 Hz, 1H), 7.50 (d, J=7.2 Hz, 1H), 7.82 (d, J=7.6 Hz, 1H), 7.85 (s, 1H); 13C NMR (DMSO-d6, 100 MHz) δ 27.45, 43.13, 119.85, 125.21, 127.11, 127.59, 129.13, 129.37, 132.61, 137.49, 140.07, 141.68, 155.73, 198.58; ESI-HRMS for C16H16N2O2Cl (M+H)+ calcd. 303.0900. found 303.0907.

後処理

  1. temperatureThe mixture was refluxed for several hours until the starting materials
  2. customwere consumed
  3. customquenched with solid NaHCO3
  4. customthe volatiles were removed under reduced pressure
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with water
  7. dry with materialThe organic layer was dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography

出典と根拠

ORDレコード
ord-aab32b7f591a4ec392ac4e45a7d95478
出典データセット
uspto-grants-2016_09
特許番号
US09447134B2

反応ノート

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