Ammonia → HCID 70417534, compound

HRID 1252267Notes

Reaction equation

HRID 1252267 reaction equation
[CH2:1]([CH2:4][C:5]12[CH2:11][CH:8]([CH:9]=[CH:10]1)[CH:7]1[C:12](O[C:15](=[O:16])[CH:6]21)=[O:13])[CH:2]=[CH2:3].[NH3:17]>>[CH2:1]([CH2:4][C:5]12[CH2:11][CH:8]([CH:9]=[CH:10]1)[CH:7]1[C:12](=[O:13])[NH:17][C:15](=[O:16])[CH:6]21)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 53956536HCID 53956536, compound

Product 1

HCID 70417534HCID 70417534, compound

Procedure

A mixture of 30 g of allylmethylbicyclo[2.2.1]-hept-5-ene-2,3-dicarboxylic anhydride, prepared in accordance with Example 2 of U.S. Pat. No. 3,105,839, and 10.2 g of 25% aqueous ammonia solution is heated at 100°-108° C. for 2.5 hours, with stirring and reflux cooling. According to a gas chromatogram, this gives a mixture of 12 isomers having varying positions for the allyl group and the methyl group in the 1-, 4-, 5- and 6-positions in the bicycloheptene ring, and also exo-anhydrides and endo-anhydrides. Since this mixture of isomers cannot be separated by fractional distillation, it is used for further purposes as such. Water is then removed by distillation, excess ammonia is expelled and the imide is rectified at 140°-145° C. and 2.0 Pa.

Workup

  1. customprepared in accordance with Example 2 of U.S
  2. temperaturereflux
  3. temperaturecooling
  4. customthis gives
  5. additionSince this mixture of isomers
  6. customcannot be separated by fractional distillation, it
  7. customWater is then removed by distillation, excess ammonia
  8. customis rectified at 140°-145° C.

Sources & evidence

ORD record
ord-ef970b4850c34828b1d3385dde8ebf8c
Source dataset
uspto-grants-1988_05
Patent number
US04742166

Reaction notes

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