2-Chloroacetamidine monohydrochloride → 2-(chloromethyl)-6,6-dimethyl-1,5,7,8-tetrahydroquinazolin-4-one

HRID 241020ノート

反応式

HRID 241020 の反応式
[CH3:1][C:2]1([CH3:13])[CH2:7][CH:6]([C:8]([O:10]C)=O)[C:5](=O)[CH2:4][CH2:3]1.Cl.[Cl:15][CH2:16][C:17](=[NH:19])[NH2:18].C[O-].[Na+]>CO>[Cl:15][CH2:16][C:17]1[N:19]=[C:8]([OH:10])[C:6]2[CH2:7][C:2]([CH3:1])([CH3:13])[CH2:3][CH2:4][C:5]=2[N:18]=1

参加物

5

反応物 3

HCID 27769572-Chloroacetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 12441545Methyl 5,5-dimethyl-2-oxocyclohexane-1-carboxylate

生成物 1

HCID 1784239482-(chloromethyl)-6,6-dimethyl-1,5,7,8-tetrahydroquinazolin-4-one収率 57%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of methyl 5,5-dimethyl-2-oxocyclohexanecarboxylate (6.0 g, 33 mmol) and 2-chloroacetimidamide hydrochloride (4.6 g, 36 mmol) in methanol (30 mL) was added sodium methoxide (4.4 M in MeOH, 9.0 mL, 40 mmol). The reaction mixture was stirred at ambient temperature for three hours and then concentrated. The resulting residue was partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. Purification by silica gel chromatography provided 2-(chloromethyl)-6,6-dimethyl-5,6,7,8-tetrahydroquinazolin-4-ol (4.2 g, 57% yield) as a white solid. MS (ES) for C11H15ClN2O: 227 (MH+).

後処理

  1. concentrationconcentrated
  2. customThe resulting residue was partitioned between ethyl acetate and aqueous sodium bicarbonate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-76e15e58c8db43899aa2f43f1eee14fe
出典データセット
uspto-grants-2014_02
特許番号
US08648066B2

反応ノート

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