Ammonia → 4-Chloro-2-[imino(phenyl)methyl]-N-methylaniline

HRID 1391208Notes

Reaction equation

HRID 1391208 reaction equation
[CH3:1][N:2]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C=O.[NH3:20]>[Cl-].[Zn+2].[Cl-].CO>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([NH:2][CH3:1])=[C:6]([CH:7]=1)[C:12](=[NH:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 20378192HCID 20378192, compound

Product 1

HCID 1512654-Chloro-2-[imino(phenyl)methyl]-N-methylanilineYield 76%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 41.1 g (0.15 mole) of N-methyl-N-(2-benzoyl-4-chlorophenyl)formamide, 90 ml methanol, 90 g anhydrous ammonia, and 0.5 g zinc chloride was heated in a sealed 360 ml Hastelloy® tube at 150° for 15 hr. and then cooled and vented. The solid portion of the residue was collected on a filter and recrystallized from methanol to give 27.8 g (76%) of 5-chloro-2-methylaminobenzophenone imine as long yellow needles: mp 93°-95°; 1H nmr (CDCl3) δ 2.92 ppm (d, J = 5.5 Hz, 3H), 6.65 ppm (d, J = 9 Hz, 1H) 7.4 ppm (m, 7H) and 9.4 ppm (broad, 2NH).

Workup

  1. temperatureand then cooled
  2. customThe solid portion of the residue was collected on
  3. filtrationa filter
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-11b0ae0fd02a4f73957fc39818a1c809
Source dataset
uspto-grants-1979_02
Patent number
US04141895

Reaction notes

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