N,N-Dimethylaniline → N-Methylformanilide

HRID 441782Notes

Reaction equation

HRID 441782 reaction equation
[CH3:1][N:2]([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:10]=O>CN(C)C=O>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 949N,N-DimethylanilineHCID 977Oxygen

Product 1

HCID 66737N-MethylformanilideYield 15.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By essentially the procedure of Example 1, a tube was charged with 20 g of dimethylaniline, 20 g of dimethylformamide, and 1.0 g of cupric chloride dihydrate. The reaction was run at 114°-115° C. for one hour while oxygen was injected incrementally at 200-400 psi. The oxygen absorption was about 0.12 mole. Analysis of the reaction mixture by GC/MS showed a 94.5% conversion of dimethylaniline and a 15.4% yield of N-methyl-N-phenylformamide.

Workup

  1. customThe oxygen absorption

Sources & evidence

ORD record
ord-8388318e24f04b6f9bedc6cdd2a9a1aa
Source dataset
uspto-grants-1977_08
Patent number
US04042621

Reaction notes

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