Dodecane → N-(3,5-dimethylphenyl)-N-methylformamide

HRID 984696Notes

Reaction equation

[O-]P([O-])([O-])=O.[K+].[K+].[K+].I[C:10]1[CH:11]=[C:12]([CH3:17])[CH:13]=[C:14]([CH3:16])[CH:15]=1.[CH3:18][NH:19][CH:20]=[O:21].CCCCCCCCCCCC>C(OCC)(=O)C.[Cu]I.C1(C)C=CC=CC=1>[CH3:16][C:14]1[CH:15]=[C:10]([N:19]([CH3:18])[CH:20]=[O:21])[CH:11]=[C:12]([CH3:17])[CH:13]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), 3,1′-dimethyl-4,5-dihydro-3H,1′H-[,2′]biimidazolyl-2-one (18 mg, 0.10 mmol, 10 mol %), K3PO4 (430 mg, 2.03 mmol), evacuated, backfilled with Ar. 5-Iodo-m-xylene (145 μL, 1.00 mmol), N-methylformamide (72 μL, 1.23 mmol), and toluene (1.0 mL) were added under Ar. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 110° C. for 24 h. The suspension was allowed to reach room temperature. Dodecane (internal GC standard, 230 μL) and ethyl acetate (2 mL) were added. A 0.1 mL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC to provide 54% yield of N-(3,5-dimethylphenyl)-N-methylformamide.

Workup

customevacuated
customThe Schlenk tube was sealed with a Teflon valve
customto reach room temperature

Sources & evidence

ORD record: ord-69742e22ed5848f2b04813027b7f9187
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867298B2

Reaction notes

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