N-Benzylformamide → N-benzyl-N-(3,5-dimethylphenyl)formamide

HRID 2179129

Reaction equation

[CH2:1]([NH:8][CH:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:12]1[CH:13]=[C:14]([CH3:19])[CH:15]=[C:16]([CH3:18])[CH:17]=1>>[CH2:1]([N:8]([C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=1)[CH:9]=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 80654N-Benzylformamide

HCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 9964751N-benzyl-N-(3,5-dimethylphenyl)formamideYield 99.2%

Procedure

Using general procedure A, N-benzylformamide (170 mg, 1.26 mmol) was coupled with 5-iodo-m-xylene (150 μL, 1.04 mmol). The crude product was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 3:1; 15 mL fractions). Fractions 7-13 provided 247 mg (99% yield) of the product as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 8.55 (s, 1H), 7.39-7.22 (m, 5H), 6.91 (s, 1H), 6.75 (s, 2H), 5.00 (s, 2H), 2.30 (s, 6H).

Workup

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

Sources & evidence

ORD record: ord-21d5589f6d6a408d8e58b3242c92519c
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067955B2

Linked notes

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