1,1'-Carbonyldiimidazole → HCID 66752059, compound

HRID 1785412Notes

Reaction equation

HRID 1785412 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]2[CH:22]=[C:21]([C:23]([OH:25])=O)[C:20]3[N:19]=[C:18]4[C:26]([CH3:30])=[CH:27][CH:28]=[CH:29][C:17]4=[CH:16][C:15]=3[C:14]2=[O:31])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH:32]1[N:36]=[CH:35][N:34]([C:37](N2C=NC=C2)=O)[CH:33]=1>C(#N)C>[CH3:35][N:34]([CH3:37])[CH2:33][CH2:32][NH:36][C:23]([C:21]1[C:20]2[N:19]=[C:18]3[C:26]([CH3:30])=[CH:27][CH:28]=[CH:29][C:17]3=[CH:16][C:15]=2[C:14](=[O:31])[N:13]([CH2:12][CH2:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:22]=1)=[O:25]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 66752063HCID 66752063, compound

Product 1

HCID 66752059HCID 66752059, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

From acid 18s with a reflux time of 48 h and a recharge with an equal amount of CDI after 24 h, and obtained as a yellow solid (81%), mp 113-114° C. (from acetonitrile). 1H NMR (CDCl3): δ 2.26 [s, 6H, N(CH3)2], 2.58 (t, J=6.5 Hz, 2H, CH2CH2NMe2), 2.77 (s, 3H, ArCH3), 3.01 (m, 2H, CH2CH2Ph), 3.67 (q, J=6.1 Hz, 2H, CH2CH2NMe2), 3.79 (s, 6H, 2×OCH3), 4.22 (m, 2H, CH2CH2Ph), 6.72-6.75 (m, 3H, H-2′, H-5′ and H-6′), 7.41 (t, J=7.6 Hz, 1H, H-8), 7.64 (d, J=6.8 Hz, 1H, H-7), 7.77 (d, J=8.2 Hz, 1H, H-9), 8.51 (s, 1H, H-3), 9.15 (s, 1H, H-10), 10.83 (br t, J=5.3 Hz, 1H, CONH).

Sources & evidence

ORD record
ord-ee4298bb91dd46e483caffa5d4745355
Source dataset
uspto-grants-2009_03
Patent number
US07504507B2

Reaction notes

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