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

HRID 502681ノート

反応式

HRID 502681 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-23928f6bb90c422091190ba4feafe47a
出典データセット
uspto-grants-2010_08
特許番号
US07776869B2

反応ノート

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