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2-Methyl-2-thiopseudourea → 2-(Methylthio)-7,8-dihydroquinazolin-5(6H)-one

HRID 2383405
ノート
印刷プレビュー

反応式

HRID 2383405 の反応式
CN([CH:4]=[C:5]1[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:6]1=O)C.C([O-])(=O)C.[Na+].[C:18]([S:21][CH3:22])(=[NH:20])[NH2:19]>CN(C=O)C.ClCCl>[CH3:22][S:21][C:18]1[N:19]=[CH:4][C:5]2[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:6]=2[N:20]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 51422-Methyl-2-thiopseudoureaHCID 3593532-[(Dimethylamino)methylidene]cyclohexane-1,3-dioneHCID 517045Sodium Acetate

生成物 1

HCID 137925232-(Methylthio)-7,8-dihydroquinazolin-5(6H)-one収率 88.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344
Dichloromethane
溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-((dimethylamino)methylene)cyclohexane-1,3-dione (0.5 g, 2.9 mmol) in DMF (2 mL) was added sodium acetate (0.39 g, 4.7 mmol) and methyl carbamimidothioate (0.9 g, 3.5 mmol). The reaction mixture was heated at 100° C. for 5 hours. On completion of the reaction, the reaction mixture was diluted with dichloromethane (30 mL). The organic layer was separated and washed with water (2×30 mL). The solvent was then removed under reduced pressure and the residue dissolved in EtOAc (50 mL) and washed with water (2×30 mL). The organic layer was dried using sodium sulfate and concentrated under reduced pressure to give the desired product (0.5 g, 86%) as a solid. 1H NMR (CDCl3, 400 MHz): δ 8.94 (s, 1H), 3.01 (t, J=6 Hz, 2H), 2.64 (t, J=6.0 Hz, 2H), 2.58 (s, 3H), 2.14 (quintet, J=6.2 Hz, 2H); LCSM [M+H]: 195.

後処理

  1. customOn completion of the reaction
  2. customThe organic layer was separated
  3. washwashed with water (2×30 mL)
  4. customThe solvent was then removed under reduced pressure
  5. dissolutionthe residue dissolved in EtOAc (50 mL)
  6. washwashed with water (2×30 mL)
  7. customThe organic layer was dried
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-58f68e4f3a2a40b4a3241bc75b59c25d
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08263610B2

反応ノート

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