Ethylene Glycol → HCID 13290481, compound

HRID 904782Notes

Reaction equation

HRID 904782 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[O:19][CH:20]([CH2:24][CH2:25][CH3:26])[C:21](=[O:23])[CH3:22].[CH2:27](O)[CH2:28][OH:29].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>C(N(CC)CC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[O:19][CH:20]([CH2:24][CH2:25][CH3:26])[C:21]1([O:29][CH2:28][CH2:27][O:23]1)[CH3:22]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 13290515HCID 13290515, compound

Product 1

HCID 13290481HCID 13290481, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 1.5 g. of N-[4-bromo-3(1-propyl-2-oxopropoxy)phenyl]-3,4,5,6-tetrahydrophthalimide, 0.7 g. of ethyleneglycol, 0.1 g. of p-toluenesulfonic acid and 30 ml. of benzene was refluxed with stirring under removing water for 5.5 hours and the reaction mixture was cooled to room temperature and 0.4 ml. of triethylamine was added. The solvent was distilled off under a reduced pressure. The residue was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane:triethylamine of 30:80:1) to obtain 1.2 g. of Compound No. 49 shown in Table 1.

Workup

  1. additionA mixture of 1.5 g
  2. distillationThe solvent was distilled off under a reduced pressure
  3. customThe residue was purified by a chromatography on a column of silica gel (developing solvent: ethyl acetate:n-hexane:triethylamine of 30:80:1)
  4. customto obtain 1.2 g

Sources & evidence

ORD record
ord-c396ba1b23a54b77a48a3e53cd5cc29f
Source dataset
uspto-grants-1983_12
Patent number
US04420327

Reaction notes

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