Benzamide → HCID 11426018, compound

HRID 1883311Notes

Reaction equation

[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:11]1[CH:22]=[CH:21][C:14]([C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])=[CH:13][CH:12]=1>>[CH2:18]([O:17][C:15]([C:14]1[CH:21]=[CH:22][C:11]([NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:12][CH:13]=1)=[O:16])[CH:19]=[CH2:20]

Participants

Reactant 2

HCID 2331Benzamide

HCID 11403485HCID 11403485, compound

Product 1

HCID 11426018HCID 11426018, compoundYield 91%

Procedure

Using general procedure A, benzamide (150 mg, 1.24 mmol) was coupled with allyl 4-iodobenzoate (300 mg, 1.04 mmol). The crude product was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 3:1; 10 mL fractions). Fractions 8-15 provided 266 mg (91% yield) of the product as white crystals. 1H NMR (400 MHz, CDCl3): δ 8.14−8.09 (m, 2H), 8.00 (br s, 1H), 7.93−7.88 (m, 2H), 7.80−7.75 (m, 2H), 7.63−7.58 (m, 1H), 7.56−7.51 (m, 2H), 6.07 (ddt, J=17.2, 11.7, 5.6 Hz, 1H), 5.45 (dq, J=17.2, 1.4 Hz, 1H), 5.32 (dq, J=11.7, 1.4 Hz, 1H), 4.85 (dt, J=5.6, 1.4 Hz, 2H).

Workup

customThe crude product was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 3:1; 10 mL fractions)

Sources & evidence

ORD record: ord-53e76f711ffc447b82d914254440abb0
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759554B2

Reaction notes

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