Cinnamaldehyde → HCID 178519048, compound

HRID 1404672Notes

Reaction equation

HRID 1404672 reaction equation
[CH:1](=[C:8]1/[N:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[NH:11][C:12]/1=[O:13])/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:22](=[O:31])/[CH:23]=[CH:24]/[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([CH:23]1[C:22](=[O:31])[O:13][C:12]2[NH:11][C:10]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[F:21])=[N:9][C:8]=2[CH:1]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 637511CinnamaldehydeHCID 136611466HCID 136611466, compound

Product 1

HCID 178519048HCID 178519048, compoundYield 62%

Procedure

Prepared according to the general procedure using (Z)-4-benzylidene-2-(2,4-difluorophenyl)-1H-imidazol-5(4H)-one and trans-cinnamaldehyde. After 72 h, the unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 5i as an off-white solid (78 mg, 62%). Analytical data for 5i: 1H NMR (500 MHz, CDCl3) δ 9.43 (d, J=7.1 Hz, 1H), 8.15 (td, J=9.0, 6.4 Hz, 1H), 7.35-7.27 (m, 5H), 7.26-7.23 (m, 1H), 7.11-7.05 (m, 2H), 7.01-6.92 (m, 3H), 6.83 (ddd, J=12.4, 8.4, 2.5 Hz, 1H), 4.09 (d, J=7.1 Hz, 1H), 3.61 (ddd, J=10.1, 6.9, 4.6 Hz, 1H), 3.34 (dd, J=14.9, 4.6 Hz, 1H), 2.42 (dd, J=14.8, 10.1 Hz, 1H); 13C NMR (CDCl3, 126 MHz) δ 169.0, 162.6 (dd, JCF=252.4, 12.8 Hz), 159.4 (dd, JCF=247.4, 11.2 Hz), 148.8, 137.9, 137.2, 136.7, 129.7 (dd, JCF=9.3, 4.8 Hz), 129.2, 129.0, 128.6, 128.3, 128.0, 126.8, 113.7 (dd, JCF=10.6, 3.5 Hz), 112.8 (dd, JCF=21.7, 3.1 Hz), 110.2 (d, JCF=3.5 Hz), 104.2 (t, JCF=26.3 Hz), 47.3, 38.4, 32.7; IR (film) cm−1 1771, 1632, 1597, 1535, 1494, 1448, 1267, 1138, 1124, 1105, 1090, 909, 850, 732, 697; LRMS (ESI): Mass calcd for [M+H]+ C25H19F2N2O2: 417.1. found 417.4; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel AD-H; 10% IPA/hexanes 1.0 mL/min, 280 nm), Rt1 (minor)=25.4 Rt2 (major)=30.9 min; er=98:2.

Workup

  1. customPrepared
  2. customthe unpurified residue was purified by flash chromatography

Sources & evidence

ORD record
ord-bfe9a78c022f444a96f9dd0a009ab7ad
Source dataset
uspto-grants-2014_12
Patent number
US08912341B2

Reaction notes

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