Urea → HCID 22013874, compound

HRID 1532732Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](O)=[O:25])=[CH:18][CH:17]=1.S(Cl)(Cl)=O.[NH2:31][C:32]([NH2:34])=[O:33]>>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][C:24]([NH:31][C:32]([NH2:34])=[O:33])=[O:25])=[CH:20][CH:21]=1

Participants

Reactant 3

HCID 1176Urea

HCID 24386Thionyl Chloride2×

HCID 10641668HCID 10641668, compound

Product 1

HCID 22013874HCID 22013874, compoundYield 50%

Conditions

Temperature: 100 °C

Procedure

To 3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionic acid (1.00 g, 2.85 mmol) obtained in Example 17 was added thionyl chloride (1.7 ml), and the mixture was stirred under heating for 1 hr at 100° C. Excess thionyl chloride was evaporated under reduced pressure and urea (257 mg, 4.28 mmol) was added to the obtained residue. The mixture was stirred under heating for 1 hr at 120° C. and purified by silica gel column chromatography (developing solvent; dichloromethane: methanol=10:1) to give the title compound (560 mg, yield 50%) as a white solid.

Workup

additionwas added to the obtained residue
stirringThe mixture was stirred
temperatureunder heating for 1 hr at 120° C.
custompurified by silica gel column chromatography (developing solvent; dichloromethane: methanol=10:1)

Sources & evidence

ORD record: ord-8dc3314deb554596bb582e3215e22397
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06204277B1

Reaction notes

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