Hexyl isocyanate → HCID 71654890, compound

HRID 1486535Notes

Reaction equation

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

Participants

Reactant 2

HCID 75659Hexyl isocyanate

HCID 2871105-Phenyluracil

Product 1

HCID 71654890HCID 71654890, compoundYield 44%

Procedure

The title compound was obtained according to the procedure described for the synthesis of Example 1, starting from 5-phenyluracil (0.05 g, 0.26 mmol); 1.8 equivalents of hexyl isocyanate were used herein. The crude was purified by silica gel column chromatography (cyclohexane:EtOAc 70:30) to afford the title compound (0.04 g, 44%) as white powder. 1H NMR (400 MHz, DMSO-d6): δ 0.87 (t, J=6.5 Hz, 3H), 1.16-1.37 (m, 6H), 1.43-1.61 (m, 2H), 3.23-3.32 (m, 2H), 7.30-7.46 (m, 3H), 7.48-7.57 (m, 2H), 8.28 (s, 1H), 9.19 (t, J=5.6, 1H), 11.94 (s, 1H). 13C NMR (101 MHz, CDCl3): δ 14.14, 22.67, 26.66, 29.31, 31.53, 41.50, 116.87, 128.53, 128.76, 131.49, 136.05, 149.92, 151.03, 161.31. MS (ESI) m/z: 333 [M-NH4]+. MS (ESI) m/z: 314 [M-H]−.

Workup

customdescribed for the synthesis of Example 1
customThe crude was purified by silica gel column chromatography (cyclohexane:EtOAc 70:30)

Sources & evidence

ORD record: ord-b8f6fee49be045aa91f6337049a968bb
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428465B2

Reaction notes

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