2-Oxopropanethioamide → 6-Bromo-4'-methyl-2-(tetrahydro-2H-pyran-3-yl)spiro[chroman-4,2'-imidazole]5'(1'H)-thione

HRID 1770967Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([CH:12]1[CH2:17][CH2:16][CH2:15][O:14][CH2:13]1)[CH2:6][C:5]2=[N:18]S(C(C)(C)C)=O.O=[C:26]([CH3:30])[C:27](=[S:29])[NH2:28]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]3([N:18]=[C:26]([CH3:30])[C:27](=[S:29])[NH:28]3)[CH2:6][CH:7]([CH:12]3[CH2:17][CH2:16][CH2:15][O:14][CH2:13]3)[O:8][C:9]2=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 130 °C

Procedure

N-(6-Bromo-2-(tetrahydro-2H-pyran-3-yl)chroman-4-ylidene)-2-methylpropane-2-sulfinamide (Example 47 Step 1, 0.5 g, 1.21 mmol) and 2-oxopropanethioamide (Intermediate 2, 0.373 g, 3.62 mmol) were dissolved in dry acetonitrile (4.0 mL) in a dry microwave vial. The vial was sealed and heated with MW for 20 min. at 130° C. The solvent was evaporated to give the crude title compound that was used directly in the next reaction. MS (ES+) m/z 395 [M+H]

Workup

customThe vial was sealed
customThe solvent was evaporated

Sources & evidence

ORD record: ord-360acc11a69745b8a234ea7d9e82bfd4
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248129B2

Reaction notes

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