p-Toluidine → 3,5-Dimethyl-N-(4-methylphenyl)benzenamine

HRID 984685Notes

Reaction equation

C(N(CC)C(=O)C1C(=CC=CC=1)O)C.[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:32]1[CH:33]=[C:34]([CH3:39])[CH:35]=[C:36]([CH3:38])[CH:37]=1.[OH-].[NH4+].CCCCCCCCCCCC>[Cu]I.O.C(OCC)(=O)C>[CH3:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:32]2[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

CuI (10 mg, 0.05 mmol), N,N-diethylsalicylamide (10 mg, 0.05 mmol), 4-toluidine (161, 1.5 mmol) and K3PO4 (425 mg, 2.0 mmol) were put into a screw-capped test tube with a Teflon-lined septum. The tube was then evacuated and backfilled with argon (3 cycles). 5-Bromo-m-xylene (136 μL, 1.0 mmol) was added by a syringe. The reaction mixture was stirred at 100° C. for 20 h. The reaction mixture was allowed to reach room temperature. Ethyl acetate (˜2 mL), water (˜10 mL), ammonium hydroxide (˜0.5 mL) and dodecane (227 μL) were added. The organic phase was analyzed by GC and 22% conversion of 5-bromo-m-xylene and 9% GC yield of the desired product was obtained.

Workup

customThe tube was then evacuated
customto reach room temperature

Sources & evidence

ORD record: ord-59a7895fa5fb4863af4ff429b735b303
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867298B2

Reaction notes

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