P-Anisidine → 2-Amino-5-(tert-butyldimethylsilyloxy)-n-(4-methoxyphenyl)benzamide

HRID 395728Notes

Reaction equation

[Si:1]([O:8][C:9]1[CH:20]=[C:13]2[C:14]([O:16]C(=O)[NH:18][C:12]2=[CH:11][CH:10]=1)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[NH2:18][C:12]1[CH:11]=[CH:10][C:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])=[CH:20][C:13]=1[C:14]([NH:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=1)=[O:16]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-(tert-butyldimethylsilyloxy)isatoic anhydride (734 mg, 2.50 mmol) and p-anisidine (339 mg, 2.75 mmol) in toluene (6 mL) was heated at 80° C. for 3 h. The reaction mixture was cooled and silica gel (3.5 g) was added. The mixture was concentrated in vacuo and the resulting material was chromatographed (silica gel, 1% ethyl acetate/99% methylene chloride to 4% ethyl acetate/96% methylene chloride) to give 547 mg (59%) of the title compound as a light tan solid; mp 82.5-83.5° C. (dec).

Workup

temperatureThe reaction mixture was cooled
additionsilica gel (3.5 g) was added
concentrationThe mixture was concentrated in vacuo
customthe resulting material was chromatographed (silica gel, 1% ethyl acetate/99% methylene chloride to 4% ethyl acetate/96% methylene chloride)

Sources & evidence

ORD record: ord-12617080cd1c4891bc722947473241db
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605626B2

Reaction notes

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