Triethylamine → HCID 12883871, compound

HRID 128403

Reaction equation

Cl[CH2:2][C:3]1[O:4][C:5](=[O:16])[N:6]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[N:7]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]([CH:28]([CH3:30])[CH3:29])[C:25]([OH:27])=[O:26])=[CH:20][CH:19]=1.C(N(CC)CC)C>C1(C)C(C)=CC=CC=1>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([CH:24]([CH:28]([CH3:30])[CH3:29])[C:25]([O:27][CH2:2][C:3]2[O:4][C:5](=[O:16])[N:6]([CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH3:15])[N:7]=2)=[O:26])=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of 2-chloromethyl-4-(2-methylbenzyl)-1,3,4-oxadiazolin-5-one (13.3 g) in xylene (35 cc) is added in the course of 20 minutes to a solution of 2-(4-chlorophenyl)-3-methyl-butyric acid (19 g) and triethylamine (11.7 cc) in xylene (175 cc) heated to 110° C. The reaction mixture is heated at the reflux temperature for 4 hours and, after cooling, is washed successively with water (100 cc), a 3.5% strength aqueous hydrochloric acid solution (100 cc), a 4% strength aqueous sodium carbonate solution (100 cc) and water (100 cc). After drying, decolorizing over animal charcoal and concentrating under reduced pressure, the residue obtained is purified by chromatography on a silica column and gives [4-(2-methylbenzyl)-1,3,4-oxadiazolin-5-on-2-yl]-methyl 2-(4-chlorophenyl)-3-methylbutyrate (11.2 g) in the form of an oil.

Workup

temperatureThe reaction mixture is heated at the reflux temperature for 4 hours
temperatureafter cooling
washis washed successively with water (100 cc)
customAfter drying
concentrationconcentrating under reduced pressure
customthe residue obtained
customis purified by chromatography on a silica column

Sources & evidence

ORD record: ord-53442acee1e346a1bf3a4760912d145e
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04259497

Linked notes

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