4-Chloroaniline → 1-(4-Chlorophenyl)-3-(3-(2-methyl-1,3-dioxolan-2-yl)benzyl)urea

HRID 64229노트

반응식

HRID 64229 반응식
[CH3:1][C:2]1([C:7]2[CH:8]=[C:9]([CH:24]=[CH:25][CH:26]=2)[CH2:10][NH:11][C:12](=[O:23])OC2C=CC([N+]([O-])=O)=CC=2)[O:6][CH2:5][CH2:4][O:3]1.[Cl:27][C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1.C(N(CC)CC)C>ClCCl>[Cl:27][C:28]1[CH:34]=[CH:33][C:31]([NH:32][C:12]([NH:11][CH2:10][C:9]2[CH:24]=[CH:25][CH:26]=[C:7]([C:2]3([CH3:1])[O:3][CH2:4][CH2:5][O:6]3)[CH:8]=2)=[O:23])=[CH:30][CH:29]=1

참가 물질

5

반응물 3

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 715005354-Nitrophenyl 3-(2-methyl-1,3-dioxolan-2-yl)benzylcarbamate

생성물 1

HCID 715005361-(4-Chlorophenyl)-3-(3-(2-methyl-1,3-dioxolan-2-yl)benzyl)urea수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-Nitrophenyl-N-benzylcarbamate 21 (267 mg, 0.767 mmol) was added to a solution of 4-chloroaniline (97 mg, 0.767 mmol) and triethylamine in dichloromethane (5 mL). The mixture was stirred at room temperature until starting materials were consumed. The reaction mixture was then diluted with dichloromethane (50 mL) and washed with aq. NaOH, water and brine. The organic layer was dried over anhydrous MgSO4, filtered and concentrated The residue was purified by column chromatography eluting with methanol/chloroform to give 22 (165 mg, 71%). 1H NMR (CDCl3, 400 MHz) δ 1.58 (s, 3H), 3.71 (t, J=6.8 Hz, 2H), 3.99 (t, J=6.8 Hz, 2H), 4.36 (d, J=5.6 Hz, 2H), 6.78 (s, 1H), 7.16-7.18 (m, 4H), 7.23-7.26 (m, 1H), 7.35 (d, J=5.6 Hz, 2H).

후처리

  1. customwere consumed
  2. additionThe reaction mixture was then diluted with dichloromethane (50 mL)
  3. washwashed with aq. NaOH, water and brine
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated The residue
  7. customwas purified by column chromatography
  8. washeluting with methanol/chloroform

출처 및 근거

ORD 기록
ord-4663fb4141974a2587606b65746737a8
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447134B2

반응 노트

불러오는 중…