Triethylamine → HCID 9944444, compound

HRID 585115Notes

Reaction equation

[C:1]1([C:7]2[O:8][C:9]([C:18]([OH:20])=O)=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C.Cl.[CH3:41][NH:42][O:43][CH3:44]>C1COCC1>[CH3:44][O:43][N:42]([CH3:41])[C:18]([C:9]1[O:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:11][C:10]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:20]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of the above-prepared 2,4-diphenyl-oxazole-5-carboxylic acid (427 mg, 1.61 mmole, 1.0 eq) in dry THF was treated with carbonyldiimidazole (340 mg, 2.09 mmole, 1.3 eq) and the mixture heated at 50° C. for 3 hours. Triethylamine (360 uL, 2.58 mmole, 1.6 eq) and N,O-dimethylhydroxylamine-HCl (236 mg, 2.42 mmole, 1.5 eq) were added and the mixture heated at 50° C. for 3 hours. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with 5% KHSO4 and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to a brown oil. The crude oil was chromatographed on silica gel eluting with (7:3) hexanes-ether to give 371 mg (75%) of the title compound as a brown crystalline solid. 1H NMR (CDCl3) δ 3.35 (s, 3H), 3.8 (s, 3H), 7.3-7.6 (m, 6H), 7.95 (dd, 2H), 8.15 (dd, 2H).

Workup

temperaturethe mixture heated at 50° C. for 3 hours
customThe mixture was partitioned between ethyl acetate and water
washThe organic phase was washed with 5% KHSO4 and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo to a brown oil
customThe crude oil was chromatographed on silica gel eluting with (7:3) hexanes-ether

Sources & evidence

ORD record: ord-8f01c1523db3415181f9919a98d19f22
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06930116B2

Reaction notes

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