Ammonia → HCID 178438297, compound

HRID 462560Notes

Reaction equation

HRID 462560 reaction equation
[CH2:1]([C:4]12[CH2:10][CH:7]([CH:8]=[CH:9]1)[CH:6]1[C:11]([O:13][C:14](=[O:15])[CH:5]21)=[O:12])[CH:2]=[CH2:3].[NH3:16]>>[CH2:1]([C:4]12[CH2:10][CH:7]([CH:8]=[CH:9]1)[CH:6]([C:11]([OH:13])=[O:12])[CH:5]2[C:14](=[NH:16])[OH:15])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 54206110Allylbicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride

Product 1

HCID 178438297HCID 178438297, compoundYield 60%

Procedure

A mixture of 102 g of allyl-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride, prepared according to Example 1 in U.S. Pat. No. 3,105,839, and 68.1 g of 25% aqueous ammonia solution is refluxed with cooling at 95°-102° C. for 70 minutes, while stirring. The water and excess ammonia are then distilled off under reduced pressure (6,133 Pa). When the internal temperature reaches 120° C., 54 ml of aqueous ammonia have been distilled off. An orange-coloured, viscous residue remains, and is distilled under a pressure of 13.3 Pa. 62.07 g of allyl-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid imide pass over between 132° and 135° C., corresponding to a yield of 60% of theory. The imide is a yellow oil of refractive index nD20 1.5421 and viscosity η25 345 Pa.s at 25° C.

Workup

  1. customprepared
  2. temperaturewith cooling at 95°-102° C. for 70 minutes
  3. distillationThe water and excess ammonia are then distilled off under reduced pressure (6,133 Pa)
  4. customreaches 120° C.
  5. distillation54 ml of aqueous ammonia have been distilled off
  6. distillationis distilled under a pressure of 13.3 Pa
  7. customover between 132° and 135° C.
  8. customat 25° C.

Sources & evidence

ORD record
ord-732e497e5428485aa8befe831c89c486
Source dataset
uspto-grants-1985_05
Patent number
US04515962

Reaction notes

Loading…