4-Acetylbenzoic Acid → HCID 67186598, compound

HRID 735885Notes

Reaction equation

[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:13]([NH2:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:25][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:10])=[CH:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 114704-Acetylbenzoic Acid

HCID 13583Dodecylamine

Product 1

HCID 67186598HCID 67186598, compoundYield 54%

Procedure

The same procedure as employed in the preparation of Example 10 (step a) but using 4-acetylbenzoic acid and dodecylamine gave the title compound as a white solid (54%). 1H NMR (CDCl3, 300 MHz) δ 8.00-7.90 (m, 2H), 7.85-7.71 (m, 2H), 6.05 (br s, 1H), 3.41-3.30 (m, 2H), 2.56 (s, 1.5H), 2.54 (s, 1.5H), 1.63-1.73 (m, 2H), 1.72-1.05 (m, 18H), 0.78 (m, 3H). M−(LC/MS(ESI)): 330.4; M+(LC/MS(ESI)): 332.4. HPLC (Condition A), Rt: 5.87 min (HPLC purity: 99.7%).

Workup

customThe same procedure as employed in the preparation of Example 10 (step a) but

Sources & evidence

ORD record: ord-6e82873f667d4599a710b84f3ee3f6c2
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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