Acetic Anhydride → (4Z)-4-(4-Cyclopropylbenzylidene)-2-[4-(2-cyclopropylethoxy)phenyl]-1,3-oxazol-5(4H)-one

HRID 456277Notes

Reaction equation

[CH:1]1([CH2:4][CH2:5][O:6][C:7]2[CH:19]=[CH:18][C:10]([C:11]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH:20]1([C:23]2[CH:28]=[CH:27][C:26](/[CH:29]=C(\NC(=O)C3C=CC(OCCC4C=CC(OC)=CC=4)=CC=3)/C(NCCO)=O)=[CH:25][CH:24]=2)[CH2:22][CH2:21]1.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>O.CCCCCC>[CH:20]1([C:23]2[CH:28]=[CH:27][C:26](/[CH:29]=[C:14]3\[N:13]=[C:11]([C:10]4[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][CH:1]5[CH2:2][CH2:3]5)=[CH:19][CH:18]=4)[O:17][C:15]\3=[O:16])=[CH:25][CH:24]=2)[CH2:22][CH2:21]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of N-[4-(2-cyclopropylethoxy)benzoyl]glycine (184 mg, 0.699 mmol) prepared in Example 9 (9b), 4-cyclopropylbenzaldehyde (113 mg, 0.769 mmol) prepared in Example 5, sodium acetate (75 mg, 0.909 mmol), and acetic anhydride (660 μL, 6.99 mmol) was stirred at 120° C. for 30 minutes and was then allowed to cool to room temperature. Hexane (2 mL) and water (4 mL) were added to the resulting solidified product which was washed by ultrasonic vibration. The precipitate was collected by filtration, washed with water and hexane, and dried by heating under reduced pressure to give 196 mg of the title compound (white powder, yield: 74%).

Workup

temperatureto cool to room temperature
washwas washed by ultrasonic vibration
filtrationThe precipitate was collected by filtration
washwashed with water and hexane
customdried
temperatureby heating under reduced pressure

Sources & evidence

ORD record: ord-b78bb6c0b3a74c9aaf6813d44e2afd66
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497397B2

Reaction notes

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