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

HRID 713399

反応式

HRID 713399 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-15e0a2eb507c40eba1e3825117b3276c
出典データセット
uspto-grants-2015_11
特許番号
US09181266B2

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