Maleic Acid → HCID 22493833, compound

HRID 2086137Notes

Reaction equation

[C:1]1([C:7]2[N:8]=[CH:9]O[C:11]=2[CH2:12][CH2:13][CH2:14][CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)/[CH:17]=[CH:18]\[C:19]([OH:21])=[O:20]>>[C:1]1([C:7]2[C:11]([CH2:12][CH2:13][CH2:14][CH3:15])=[C:18]([CH:17]=[CH:9][N:8]=2)[C:19]([OH:21])=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 444266Maleic Acid

HCID 22493735HCID 22493735, compound

Product 1

HCID 22493833HCID 22493833, compound

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-phenyl-5-butyloxazole (12,5 g, 25 mmol) and maleic acid (3.5 g, 30 mmol) is heated at 100° C. for 30 min. After cooling, the semisolid mass is triturated with ether and the solid collected by filtration. 1H NMR (δ, CDCl3, 400 MHz) 11.68 (brs, 1H), 8.72 (d, J=6.0 Hz, 1H), 7.73 (d, J=5.6 Hz, 1H), 7.48-7.51 (m, 2H), 7.42-7.44 (m, 2H), 6.25 (s, 1H), 2.86 (d, J=7.6 Hz, 2H), 1.36 (m, 2H), 1.11 (dt, J=7.6, 7.2 Hz, 2H), 0.68 (t, J=7.6 Hz, 3H). MS (M+1): 256, (M−1) 254.

Workup

temperatureAfter cooling
customthe semisolid mass is triturated with ether
filtrationthe solid collected by filtration

Sources & evidence

ORD record: ord-23fc12de7bc1412c9b115c0c446fcac6
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06723743B1

Reaction notes

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