3,4,5,6-Tetrahydrophthalic anhydride → HCID 13121827, compound

HRID 904779Notes

Reaction equation

HRID 904779 reaction equation
[C:1]12[C:10](=[O:11])[O:9][C:7](=O)[C:2]=1[CH2:3][CH2:4][CH2:5][CH2:6]2.[Cl:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=1[O:20][CH:21]1[CH2:25][CH2:24][CH2:23][C:22]1=[O:26]>C(O)(=O)C>[Cl:12][C:13]1[CH:19]=[CH:18][C:16]([N:17]2[C:10](=[O:11])[C:1]3[CH2:6][CH2:5][CH2:4][CH2:3][C:2]=3[C:7]2=[O:9])=[CH:15][C:14]=1[O:20][CH:21]1[CH2:25][CH2:24][CH2:23][C:22]1=[O:26]

Participants

4

Reactant 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 13121826HCID 13121826, compound

Product 1

HCID 13121827HCID 13121827, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.52 g. of cyclohexene-1,2-dicarboxylic anhydride, 2.26 g. of 4-chloro-3-(cyclopentanon-2-yloxy) aniline and 10 ml. of acetic acid was stirred at room temperature for 30 minutes and then was refluxed with stirring for 2.5 hours. The solvent was distilled off under a reduced pressure and then, ethyl acetate was added to the residue to extract the product. The extract was washed with water and dehydrated over sodium sulfate. The solvent was distilled off and the product was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane of 1:4) to obtain Compound No. 5 shown in Table 1.

Workup

  1. additionA mixture of 1.52 g
  2. temperaturewas refluxed
  3. distillationThe solvent was distilled off under a reduced pressure
  4. additionethyl acetate was added to the residue
  5. extractionto extract the product
  6. washThe extract was washed with water
  7. distillationThe solvent was distilled off
  8. customthe product was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane of 1:4)
  9. customto obtain Compound No

Sources & evidence

ORD record
ord-0b366377ba6149a9a42569b5fac5d994
Source dataset
uspto-grants-1983_12
Patent number
US04420327

Reaction notes

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