4-Fluorobenzoyl isothiocyanate → tert-Butyl 2-(3-(4-fluorobenzoyl)thioureido)-5,5-dimethyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate

HRID 1616702Notes

Reaction equation

[NH2:1][C:2]1[S:12][C:5]2[CH2:6][O:7][C:8]([CH3:11])([CH3:10])[CH2:9][C:4]=2[C:3]=1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[F:20][C:21]1[CH:31]=[CH:30][C:24]([C:25]([N:27]=[C:28]=[S:29])=[O:26])=[CH:23][CH:22]=1>C1COCC1>[F:20][C:21]1[CH:31]=[CH:30][C:24]([C:25]([NH:27][C:28](=[S:29])[NH:1][C:2]2[S:12][C:5]3[CH2:6][O:7][C:8]([CH3:11])([CH3:10])[CH2:9][C:4]=3[C:3]=2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:26])=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

tert-Butyl 2-amino-5,5-dimethyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (0.28 g, 1.00 mmol) and 4-fluorobenzoyl isothiocyanate (0.18 g, 0.99 mmol) were dissolved in THF (5 mL) and heated at 50° C. for 22 hours. The solvent was removed and EtOH (10 mL) was added. The product was filtered and rinsed with EtOH (2×10 mL). tert-Butyl 2-(3-(4-fluorobenzoyl)thioureido)-5,5-dimethyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (0.330 g, 0.71 mmol, 71% yield) was isolated as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 14.70 (s, 1H), 9.01 (s, 1H), 8.00-7.94 (m, 2H), 7.25-7.18 (m, 2H), 4.74 (apparent t, J=1.5 Hz, 2H), 2.76 (apparent t, J=1.5 Hz, 2H), 1.64 (s, 9H), 1.31 (s, 6H).

Workup

customThe solvent was removed
additionEtOH (10 mL) was added
filtrationThe product was filtered
washrinsed with EtOH (2×10 mL)

Sources & evidence

ORD record: ord-3ec6fdf4184a40faa5e8b75c7fe53b9b
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765803B1

Reaction notes

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