4-Acetylbenzoic Acid → HCID 10096037, compound

HRID 10687Notes

Reaction equation

[CH:1]([C:3]1[CH:15]=[C:14]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[C:13]([O:21][CH3:22])=[CH:12][C:4]=1[O:5][CH2:6][C:7]([N:9]([CH3:11])[CH3:10])=[O:8])=O.[C:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=1)(=[O:25])[CH3:24]>>[CH3:10][N:9]([CH3:11])[C:7]([CH2:6][O:5][C:4]1[CH:12]=[C:13]([O:21][CH3:22])[C:14]([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[CH:15][C:3]=1/[CH:1]=[CH:24]/[C:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=1)=[O:25])=[O:8]

Participants

Reactant 2

HCID 114704-Acetylbenzoic Acid

HCID 219809992-(2-formyl-5-methoxy-4-thiophen-2-yl-phenoxy)-N,N-dimethyl-acetamide

Product 1

HCID 10096037HCID 10096037, compoundYield 75%

Procedure

The title compound was prepared by condensing 2-(2-formyl-5-methoxy-4-thiophen-2-yl-phenoxy)-N,N-dimethyl-acetamide (Ex-67A) and 4-acetylbenzoic acid in a similar manner as described in Ex-3. Yellow solid, mp 228–229° C., 75% yield. 1H-NMR (300 MHz, DMSO-d6) δ 8.31 (d, 2H, J=9.3 Hz), 8.22 (d, 2H, J=13.3 Hz), 8.08 (d, 2H, J=9.3 Hz), 7.95 (s, 1H), 7.65 (d, 1H, J=2.7 Hz), 7.52 (d, 1H, J=5.1 Hz), 7.13 (dd, 1H, J=5.1, 2.7 Hz), 6.85 (s, 1H), 5.11 (s, 2H), 3.99 (s, 3H), 3.06 (s, 3H), 2.93 (s, 3H). MS (EI) m/z=465 ([M]+, 100%). HRMS (EI) Calcd. for C25H23NO6S: 465.1246. Found: 465.1246.

Sources & evidence

ORD record: ord-ac9418c514e14ffda68996d6b85f8680
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094801B2

Reaction notes

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