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

HRID 2383405Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-58f68e4f3a2a40b4a3241bc75b59c25d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263610B2

Reaction notes

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