4-Chlorobenzoyl chloride → 4-Chloro-N-(3-[1,3]dioxolan-2-yl-phenyl)-benzamide

HRID 1486718노트

반응식

HRID 1486718 반응식
[CH2:1]1[O:12][CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=2)[O:3][CH2:2]1.[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>C(OCC)(=O)C>[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([CH:4]3[O:3][CH2:2][CH2:1][O:12]3)[CH:6]=2)=[O:19])=[CH:16][CH:15]=1

참가 물질

4

반응물 2

HCID 85014-Chlorobenzoyl chlorideHCID 70203623-(1,3-Dioxolan-2-yl)aniline

생성물 1

HCID 867065474-Chloro-N-(3-[1,3]dioxolan-2-yl-phenyl)-benzamide수율 78%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

A solution of 3-aminobenzaldehyde ethylene acetal (10 g, 60.5 mmol) and TEA (7.35 g, 72.6 mmol) in ethyl acetate (100 mL) at 0° C. is treated dropwise with 4-chlorobenzoyl chloride (9.44 mL, 72.6 mmol) during 30 min. The reaction mixture is stirred at RT for 3 h before dilution with EtOAc. The medium is washed twice with sat. aq. NaHCO3 (100 mL) and once with brine (100 mL). The organic layer is dried over MgSO4, filtered and evaporated. The residual oil is triturated with ethyl acetate and the resulting crystalline material is filtered to give the title compound (14.33 g, 78%) as a slightly pink solid; LC-MS B: tR=0.86 min; [M+H]+=304.03.

후처리

  1. washThe medium is washed twice with sat. aq. NaHCO3 (100 mL) and once with brine (100 mL)
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residual oil is triturated with ethyl acetate
  6. filtrationthe resulting crystalline material is filtered

출처 및 근거

ORD 기록
ord-9d57be9c7c424d10aebaf36ad488450a
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428456B2

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