Ethanethiol → HCID 22118267, compound

HRID 1274872Notes

Reaction equation

[CH2:1]([SH:3])[CH3:2].[CH3:4][C:5]1[O:10][CH2:9][N:8]([C:11]([CH3:17])([CH3:16])[C:12](=[O:15])[CH:13]=[CH2:14])[C:7](=[O:18])[C:6]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([S:3][CH2:14][CH2:13][C:12](=[O:15])[C:11]([N:8]1[C:7](=[O:18])[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:5]([CH3:4])[O:10][CH2:9]1)([CH3:17])[CH3:16])[CH3:2]

Participants

Conditions

Temperature: 20 °C

Procedure

Ethanethiol (0.0389 ml) was added to a mixture of 4-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-4-methylpent-1-en-3-one (100 mg) and potassium carbonate (4.85 mg) in N,N-dimethylformamide, and then stirred overnight at 20° C., and for 24 hours at 40° C. The mixture was purified by silica gel column chromatography eluting with isohexane/ethyl acetate (4:1) to give 5-ethylthio-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpentan-3-one (Compound 1083, 45 mg), NMR 1.2(t,3H), 1.4(s,6H), 1.9(s,3H), 2.5(q,2H), 2.8(s,4H), 5.3(s,2H),7.2-7.4(m,5H).

Workup

waitfor 24 hours at 40° C
customThe mixture was purified by silica gel column chromatography
washeluting with isohexane/ethyl acetate (4:1)

Sources & evidence

ORD record: ord-466a68ffcd0945c38d6378829ad628cb
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06159902

Reaction notes

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