Triethylamine → 2-(chloromethyl)-5,6,7,8-tetrahydroquinazolin-4(3H)-one

HRID 713399노트

반응식

HRID 713399 반응식
CCO[C:4]([CH:6]1[C:11](=O)[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].Cl.[Cl:14][CH2:15][C:16]([NH2:18])=[NH:17].C(N(CC)CC)C>CO>[Cl:14][CH2:15][C:16]1[NH:18][C:4](=[O:5])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[N:17]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 27769572-Chloroacetamidine monohydrochloride

생성물 1

HCID 1354490022-(chloromethyl)-5,6,7,8-tetrahydroquinazolin-4(3H)-one수율 13%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of ethyl 2-cyclohexanone-carboxylate (5.5 g, 32 mmol) in methanol was added chloroacetamidine hydrochloride (4.2 g, 32 mmol) and triethylamine (14 mL, 97 mmol). The mixture was stirred at ambient temperature for 60 h. It was then concentrated under reduced pressure and purified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0) to provide product (0.82 g, 13% yield). 1H NMR (400 MHz, CD3OD) δ 4.40 (s, 2H), 2.61 (t, J=6.3 Hz, 2H), 2.45 (t, J=6.3 Hz, 2H), 1.68-1.87 (m, 4H). MS m/z 199.2 (M+1), retention time=0.94 min.

후처리

  1. concentrationIt was then concentrated under reduced pressure
  2. custompurified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0)

출처 및 근거

ORD 기록
ord-15e0a2eb507c40eba1e3825117b3276c
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181266B2

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