Ethanol → HCID 44468077, compound

HRID 1642418Notes

Reaction equation

HRID 1642418 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:19][CH:18]=[CH:17][N:5]2[C:6](=[O:16])[C:7]=1[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.CO[CH:22]([CH2:34][CH3:35])[CH:23]([O:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=O)C.[O-:36][CH2:37]C.[Na+].[CH2:40](O)C>>[CH3:37][O:36][C:33]1[C:26]([O:25][CH2:23][CH2:22][CH2:34][CH2:35][CH3:40])=[C:27](/[CH:28]=[CH:1]/[C:2]2[N:3]=[C:4]3[S:19][CH:18]=[CH:17][N:5]3[C:6](=[O:16])[C:7]=2[C:8]2[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=2)[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 66752927HCID 66752927, compoundHCID 86636076HCID 86636076, compound

Product 1

HCID 44468077HCID 44468077, compound

Procedure

The title compound was prepared from Intermediate 4 (400 mg, 1.4 mmol), (3-methoxy-2-pentyloxy)benzaldehyde (498 mg, 2.22 mmol) and sodium ethoxide (190 mg, 2.8 mmol) in ethanol (25 ml) according to procedure described in Example 9 to give 300 mg of the product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 0.90-1.00 (m, 3H), 1.25-1.45 (m, 4H), 1.46-1.60 (m, 2H), 3.77 (s, 3H), 3.65-3.85 (m, 2H), 6.87 (d, J=16.2 Hz, 1H), 6.96-7.00 (m, 3H), 7.54-7.57 (m, 3H), 7.93 (d, J=7.5 Hz, 1H), 8.00-8.01 (m, 2H), 8.09 (d, J=14.7 Hz, 1H); ESI-MS (m/z) 472.27 (M+H)+.

Sources & evidence

ORD record
ord-5b404750a70c44f3a03b648dc1ee083b
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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