Dimethylformamide dimethyl acetal → HCID 58031425, compound

HRID 2067626Notes

Reaction equation

[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[C:10]2=[O:25])=[N:6][C:5]=1[CH3:26])(=[O:3])[CH3:2].CO[CH:29](OC)[N:30]([CH3:32])[CH3:31]>CN(C)C=O>[CH3:29][N:30]([CH3:32])/[CH:31]=[CH:2]/[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:24])[F:23])=[CH:17][CH:16]=3)[C:10]2=[O:25])=[N:6][C:5]=1[CH3:26])=[O:3]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 1-(5-acetyl-4-methylthiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)-imidazolidin-2-one (1.00 g, 2.60 mmol) in N,N-dimethylformamide (20 mL) was added N,N-dimethylformamide dimethyl acetal (0.45 mL, 3.17 mmol). The reaction mixture was heated at 110° C. for 18 hours. The solvent was removed in vacuo, and the residue was washed with water to afford the title compound in 98% yield (1.12 g): 1H NMR (300 MHz, DMSO-d6) δ 7.70 (d, J=8.1 Hz, 2H), 7.60 (d, J=8.1 Hz, 2H), 7.58 (d, J=12.0 Hz, 1H), 5.28 (d, J=12.0 Hz, 1H), 4.50 (s, 2H), 4.01-3.95 (m, 2H), 3.48-3.43 (m, 2H), 3.08 (s, 3H), 2.81 (s, 3H), 2.48 (s, 3H); MS (ES+) m/z 439.1 (M+1).

Workup

customThe solvent was removed in vacuo
washthe residue was washed with water

Sources & evidence

ORD record: ord-68660dcca092497eb5785d1f0cd9fc73
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293768B2

Reaction notes

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