3,5-Dichloroaniline → HCID 178431743, compound

HRID 1702772Notes

Reaction equation

HRID 1702772 reaction equation
[CH3:1][C:2]12[C:9](=[O:10])[O:8][C:6](=[O:7])[CH:3]1[CH2:4][CH2:5]2.[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[NH2:15]>C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:13]=[C:14]([N:15]=[C:9]([C:2]2([CH3:1])[CH2:5][CH2:4][CH:3]2[C:6]([OH:8])=[O:7])[OH:10])[CH:16]=[C:17]([Cl:19])[CH:18]=1

Participants

4

Reactant 2

HCID 122813,5-DichloroanilineHCID 1235636764197-91-7

Product 1

HCID 178431743HCID 178431743, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10 g (0.07 mol) of 1-methyl-cyclobutane-1,2-dicarboxylic acid anhydride are dissolved in 50 ml of toluene, and 11.6 g (0.07 mol) of 3,5-dichloroaniline are added. After 24 hours' stirring at room temperature, the amide acid (m.p. 106°-108° C.) which has precipitated is separated. This amidocarboxylic acid is suspended in 40 ml of acetic anhydride, and the suspension is stirred for 24 hours at room temperature, in the course of which everything goes into solution. The acetic anhydride is evaporated off in a water-jet vacuum, and the pulverulent residue is recrystallised from dichloromethane/n-hexane to yield 15 g (73% of theory) of 1-methyl-cyclobutane-1,2-dicarboxylic acid-(3,5-dichlorophenyl)-imide, m.p. 110°-111° C. NMR Spectrum (100 MHz) δ in ppm: 1.55 (s, 3H, CH3), 2.0-3.2 (m, 5H, --CH2CH2 --CH--), 7.2-7.5 (m, 3H, aromat.). Compound No. 7.

Workup

  1. customthe amide acid (m.p. 106°-108° C.) which has precipitated
  2. customis separated
  3. stirringthe suspension is stirred for 24 hours at room temperature, in the course of which everything
  4. customThe acetic anhydride is evaporated off in a water-jet vacuum
  5. customthe pulverulent residue is recrystallised from dichloromethane/n-hexane

Sources & evidence

ORD record
ord-0112d0e1a0444a9bbf3252e3789e69e2
Source dataset
uspto-grants-1982_09
Patent number
US04349564

Reaction notes

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