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

HRID 1616704Notes

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].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=1)[C:25]([N:27]=[C:28]=[S:29])=[O:26]>C1COCC1>[C:16]([O:15][C:13]([C:3]1[C:4]2[CH2:9][C:8]([CH3:11])([CH3:10])[O:7][CH2:6][C:5]=2[S:12][C:2]=1[NH:1][C:28]([NH:27][C:25](=[O:26])[C:24]1[CH:30]=[CH:31][CH:32]=[C:22]([O:21][CH3:20])[CH:23]=1)=[S:29])=[O:14])([CH3:19])([CH3:18])[CH3:17]

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 3-methoxybenzoyl isothiocyanate (0.20 g, 1.01 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-(3-methoxybenzoyl)thioureido)-5,5-dimethyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (0.32 g, 0.68 mmol, 68% yield) was isolated as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 14.71 (s, 1H), 9.06 (s, 1H), 7.51-7.49 (m, 1H), 7.44-7.40 (m, 2H), 7.19-7.13 (m, 1H), 4.74 (apparent t, J=1.5 Hz, 2H), 3.89 (s, 3H), 2.77 (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-55ab10103bfc4f3391b9ac09a60a3015
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765803B1

Reaction notes

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