3,5-Dichloroaniline → HCID 68540128, compound

HRID 1730642Notes

Reaction equation

HRID 1730642 reaction equation
[CH:1]12[CH2:14][CH2:13][CH:5]([CH:6]3[C:11](=[O:12])[O:10][C:8](=O)[CH:7]31)[CH:4]1[CH:2]2[CH2:3]1.C1CC=CC=CC=1.C1(=O)OC(=O)C=C1.[Cl:29][C:30]1[CH:31]=[C:32]([CH:34]=[C:35]([Cl:37])[CH:36]=1)[NH2:33]>C1(C)C=CC=CC=1>[Cl:29][C:30]1[CH:31]=[C:32]([N:33]2[C:8](=[O:10])[CH:7]3[CH:6]([CH:5]4[CH2:13][CH2:14][CH:1]3[CH:2]3[CH:4]4[CH2:3]3)[C:11]2=[O:12])[CH:34]=[C:35]([Cl:37])[CH:36]=1

Participants

5

Reactant 3

HCID 122813,5-DichloroanilineHCID 54134744HCID 54134744, compoundHCID 86734205HCID 86734205, compound

Product 1

HCID 68540128HCID 68540128, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

19.2 g of tricyclo-[3.2.2.02.4 ]-nonane-6,7-dicarboxylic acid anhydride (prepared from the cycloheptatriene/maleic acid anhydride adduct (see Ex. 1a) by catalytic hydrogenation, K. Alder, Ber. 86, 1528-39 (1953) and 19.4 g of 3,5-dichloroaniline are refluxed in 1000 ml of toluene for 16 hours, whereby thewater forming during the reaction is separated with a water separator. After cooling, the toluene is removed in vacuum, and the residue recrystallised from ethyl acetate, M.P. 145° - 153° C.

Workup

  1. customwhereby thewater forming during the reaction
  2. customis separated with a water separator
  3. temperatureAfter cooling
  4. customthe toluene is removed in vacuum
  5. customthe residue recrystallised from ethyl acetate, M.P. 145° - 153° C.

Sources & evidence

ORD record
ord-2d77e6d178894028b56d89afd524e95f
Source dataset
uspto-grants-1976_11
Patent number
US03993662

Reaction notes

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