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

HRID 1243124Notes

Reaction equation

[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN(C)P(N(C)C)N(C)C.I[C:20]1[CH:21]=[C:22]([CH3:27])[CH:23]=[C:24]([CH3:26])[CH:25]=1.[CH3:28][NH:29][CH:30]=[O:31].CCCCCCCCCCCC>C(OCC)(=O)C.[Cu]I.C1(C)C=CC=CC=1>[CH3:26][C:24]1[CH:25]=[C:20]([N:29]([CH3:28])[CH:30]=[O:31])[CH:21]=[C:22]([CH3:27])[CH:23]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A Schlenk tube was charged with CuI (9.6 mg, 0.050 mmol, 5.0 mol %), K3PO4 (430 mg, 2.03 mmol), evacuated, backfilled with Ar. Hexamethylphosphorous triamide (18.5 μL, 0.102 mmol, 10 mol %) 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 76% 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-a086cf3c3a7c445b815a3c5fec91c8e9
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115784B2

Reaction notes

Loading…