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

HRID 2383405
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HRID 2383405 반응식
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
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344
Dichloromethane
용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-58f68e4f3a2a40b4a3241bc75b59c25d
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08263610B2

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