4-(4-Acetamidophenyl)-2-amino-3-cyanofurane → 4-(4-Acetamidophenyl)-3-cyano-2-[(ethoxymethylidene)amino]furane

HRID 32473Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:17]#[N:18])=[C:13]([NH2:16])[O:14][CH:15]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>C(OCC)(OCC)OCC.C(OC(=O)C)(=O)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:12]([C:17]#[N:18])=[C:13]([N:16]=[CH:15][O:14][CH2:13][CH3:12])[O:14][CH:15]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 4-(4-acetamidophenyl)-2-amino-3-cyanofurane 5 (7.64 g, 39 mmol) in triethyl orthoformate (306 mL), acetic anhydride (15 mL) was added at room temperature. The mixture was heated (inner temp: 100° C.) in an oil bath for 1 h. The black material was precipitated in the mixture and then filtrated. The filtrated material was purified on a silica gel column (eluted by n-hexane-EtOAc 1:3) to afford 473 mg of 6 as a yellow solid. The filtered solution was concentrated in vacuo to afford 6 (7.44 g) as a dark orange solid.

Workup

additionwas added at room temperature
customThe black material was precipitated in the mixture
filtrationfiltrated
customThe filtrated material was purified on a silica gel column (eluted by n-hexane-EtOAc 1:3)

Sources & evidence

ORD record: ord-6d98731f6fc1489a835fa7be02bd17b3
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427623B2

Reaction notes

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