Acetaminophen → HCID 67525990, compound

HRID 133766Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[F:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]2([CH3:25])[CH2:24][O:23]2)=[O:21])=[CH:15][C:14]=1[CH3:26]>>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:25][C:22]([OH:23])([CH3:24])[C:20]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([F:12])=[C:14]([CH3:26])[CH:15]=2)=[O:21])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 1983Acetaminophen

HCID 45097138HCID 45097138, compound

Product 1

HCID 67525990HCID 67525990, compound

Procedure

3-(4-Acetylaminophenoxy)-N-(4-fluoro-3-methylphenyl)-2-hydroxy-2-methylpropionamide was prepared as described in Example 61 c starting from 4-acetamidophenol and 2-methyloxirane-2-carboxylic acid (4-fluoro-3-methylphenyl)amide. 1H NMR (400 MHz, DMSO-d6): 1.40 (3H, s), 2.00 (3H, s), 2.20 (3H, s), 3.90 (1H, d, J=9.5 Hz), 4.15 (1H, d, J=9.5 Hz), 6.03 (1H, s), 6.84 (2H, d, J=8.7 Hz), 7.03-7.08 (1H, m), 7.44 (2H, d, J=8.7 Hz), 7.54-7.57 (1H, m), 7.67-7.69 (1H, m), 9.62 (1H, s), 9.75 (1H, s).

Sources & evidence

ORD record: ord-a56dc0aef1554be0b435d57bd541f38f
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390923B2

Reaction notes

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