2,4,6-Trimethylaniline → PhCH(CH3)NHMes

HRID 341358

Reaction equation

HRID 341358 reaction equation
[C:1]1([CH3:10])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH2:9].[C:11](OOC(C)(C)C)(C)(C)[CH3:12].Cl[C:22]1[CH:27]=[C:26](Cl)[C:25](Cl)=[CH:24][C:23]=1Cl>C(C1C=CC=CC=1)C>[C:22]1([CH:11]([NH:9][C:2]2[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=2[CH3:10])[CH3:12])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 69132,4,6-TrimethylanilineHCID 72701,2,4,5-TetrachlorobenzeneHCID 8033Di-tert-butyl peroxide

Product 1

HCID 12023477PhCH(CH3)NHMes

Reagents, catalysts & solvents 1

HCID 7500EthylbenzeneSolvent

Procedure

To a solution of 104 μL, (100 mg; 0.741 mmol) of mesitylamine, 136 μL, (108 mg; 0.741 mmol) t-butyl peroxide, 20 mL (neat) ethylbenzene was added the appropriate amount of {[Cl2NNF6Cu]}2(C6H6) from a stock solution in benzene. The reaction mixture was allowed to react inside a sealed pressure vessel and allowed to react at the specified temperature and time. Yields were determined via 1H NMR using 1,2,4,5-tetrachlorobenzene as a standard. See FIGS. 22 and 23. 1H NMR (benzene-d6, RT): δ 7.105 (m, 7, Ar—H), 4.159 (m, 1, CBz—H), 2.907 (br, 1, N—H), 2.142 (s, 3, p-CH3), 2.040 (s, 6, o-CH3), 1.341 (d, 3, CH3); m/z=240 (CI mode); byproduct diazene MesN═NMes 1H NMR (benzene-d6): δ 6.742 (s, 4, Ar—H), 2.461 (s, 12, o-CH3), 2.116 (s, 6, p-CH3); m/z=267 (CI mode).

Workup

  1. customto react inside a sealed pressure vessel
  2. customto react at the specified temperature and time
  3. customYields

Sources & evidence

ORD record
ord-2204d92ff9bd44ec97e7d61c1ea873f2
Source dataset
uspto-grants-2014_11
Patent number
US08895781B2

Linked notes

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