Thionyl Chloride → N-Cyclopropyl-3-iodo-4-methylbenzamide

HRID 502681노트

반응식

HRID 502681 반응식
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=O.S(Cl)(Cl)=O.CC[N:18]([CH:22]([CH3:24])[CH3:23])C(C)C.C1(N)CC1>C(Cl)Cl.CCOC(C)=O>[CH:22]1([NH:18][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][C:10]([CH3:11])=[C:2]([I:1])[CH:3]=2)[CH2:24][CH2:23]1

참가 물질

7

반응물 4

HCID 24386Thionyl ChlorideHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 6216403-Iodo-4-methylbenzoic acid

생성물 1

HCID 21914546N-Cyclopropyl-3-iodo-4-methylbenzamide

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To 3-iodo-4-methylbenzoic acid (3.5 g, 13 mmol) was added thionyl chloride (10 mL) before heating the mixture to reflux for 1.5 h. The reaction mixture was concentrated in vacuo, and dissolved in DCM (50 mL) and Hünigs base (4.6 mL, 27 mmol). After the addition of cyclopropylamine (1.87 mL, 27 mmol) at −78° C., the reaction mixture was stirred at ambient Temp. for about 3 h. The mixture was diluted with 100 mL DCM, washed with 20 mL saturated, aqueous NaHCO3 and 20 mL 3 N HCl, and dried over anhydrous Na2SO4. The solid obtained was suspended in EtOAc and filtered to give the title compound. MS (ES+): 302 (M+H)+.

후처리

  1. temperaturebefore heating the mixture
  2. temperatureto reflux for 1.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. dissolutiondissolved in DCM (50 mL)
  5. washwashed with 20 mL saturated
  6. dry with materialaqueous NaHCO3 and 20 mL 3 N HCl, and dried over anhydrous Na2SO4
  7. customThe solid obtained
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-23928f6bb90c422091190ba4feafe47a
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776869B2

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