Water → N-(4-chloro-2-fluoro-5-isopropoxyphenyl)-3-methyl-3,4,5,6-tetrahydrophthalic acid imide

HRID 2165503Notes

Reaction equation

HRID 2165503 reaction equation
[CH3:1][CH:2]1[CH2:12][CH2:11][CH2:10][C:4]2[C:5]([O:7][C:8](=[O:9])[C:3]1=2)=O.[Cl:13][C:14]1[C:20]([O:21][CH:22]([CH3:24])[CH3:23])=[CH:19][C:17]([NH2:18])=[C:16]([F:25])[CH:15]=1.O>C1(C)C=CC=CC=1.CN(C1C=CC=CN=1)C>[Cl:13][C:14]1[C:20]([O:21][CH:22]([CH3:24])[CH3:23])=[CH:19][C:17]([N:18]2[C:8](=[O:9])[C:3]3[CH:2]([CH3:1])[CH2:12][CH2:11][CH2:10][C:4]=3[C:5]2=[O:7])=[C:16]([F:25])[CH:15]=1

Participants

6

Reactant 3

HCID 962WaterHCID 158649Benzenamine, 4-chloro-2-fluoro-5-(1-methylethoxy)-HCID 101301323-Methyl-3,4,5,6-tetrahydrophthalic acid anhydride

Product 1

HCID 17801969N-(4-chloro-2-fluoro-5-isopropoxyphenyl)-3-methyl-3,4,5,6-tetrahydrophthalic acid imideYield 82%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 1140TolueneSolvent

Procedure

15.4 g (0.093 mol) of 3-methyl-3,4,5,6-tetrahydrophthalic acid anhydride are dissolved in 90 ml of toluene. 18.4 g (0.093 mol) of 4-chloro-2-fluoro-5-isopropoxyaniline and 0.6 g of dimethylaminopyridine are added and the mixture is heated until the solvent and the water that has formed distil off. After approximately 2 hours at a bath temperature of 145° C. the reaction is complete. The residue is chromatographed over a column of silica gel with hexane/ethyl acetate 9:1. As main fraction there are obtained 26.8 g (82.0%) of the title compound (Compound No. 1.030) of the formula ##STR9## in the form of an oil, nD22 =1.5458.

Workup

  1. temperaturethe mixture is heated until the solvent
  2. customdistil off
  3. customThe residue is chromatographed over a column of silica gel with hexane/ethyl acetate 9:1

Sources & evidence

ORD record
ord-5be03feda2ac4888b87ca42f7a75ef40
Source dataset
uspto-grants-1990_07
Patent number
US04940485

Reaction notes

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