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

HRID 241020노트

반응식

HRID 241020 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-76e15e58c8db43899aa2f43f1eee14fe
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648066B2

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