4-Chlorobenzaldehyde → (4Z)-4-(4-Chlorobenzylidene)-2-{4-[2-(4-methoxyphenyl)ethoxy]phenyl}-1,3-oxazol-5(4H)-one

HRID 1099541

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N-{4-[2-(4-methoxyphenyl)ethoxy]benzoyl}glycine (329 mg, 1.00 mmol) prepared in Example 1 (1b), 4-chlorobenzaldehyde (148 mg, 1.05 mmol), sodium acetate (111 mg, 1.35 mmol), and acetic anhydride (467 μL, 5.00 mmol) was stirred at 120° C. for 20 minutes, and then water was added thereto to terminate the reaction. Then, continuously, the mixture was vigorously stirred until the mixture was cooled to room temperature. The deposited precipitate was collected by filtration, washed with water and hexane, and dried by heating under reduced pressure to give 376 mg of the title compound (yellow powder, yield: 87%).

Workup

customto terminate
customthe reaction
stirringThen, continuously, the mixture was vigorously stirred until the mixture
temperaturewas cooled to room temperature
filtrationThe deposited precipitate was collected by filtration
washwashed with water and hexane
customdried
temperatureby heating under reduced pressure

Sources & evidence

ORD record: ord-6ed5f4a708ff427188f3cc13939949a5
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143446B2

Linked notes

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