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

HRID 456268

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-3671a4b7833f475f8680cd21514b8701
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497397B2

Linked notes

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