Methyl iodide → HCID 23181677, compound

HRID 2165504Notes

Reaction equation

HRID 2165504 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:13](=[O:14])[C:12]3[CH:15]([CH3:19])[CH2:16][CH2:17][CH2:18][C:11]=3[C:10]2=[O:20])=[C:4]([F:21])[CH:3]=1.[C:22](=O)([O-])[O-].[K+].[K+].CI>C(C(C)=O)CC>[Cl:1][C:2]1[C:7]([O:8][CH3:22])=[CH:6][C:5]([N:9]2[C:13](=[O:14])[C:12]3[CH:15]([CH3:19])[CH2:16][CH2:17][CH2:18][C:11]=3[C:10]2=[O:20])=[C:4]([F:21])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 17801971HCID 17801971, compound

Product 1

HCID 23181677HCID 23181677, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 78952-PentanoneSolvent

Conditions

Temperature
45 °C

Procedure

6.1 g (0.02 mol) of N-(4-chloro-2-fluoro-5-hydroxyphenyl)-3-methyl-3,4,5,6-tetrahydrophthalic acid imide are heated at 80° C. together with 3.0 g (0.022 mol) of potassium carbonate in 50 ml of methyl propyl ketone. After 30 minutes thick salt is precipitated. 1.5 ml (0.024 mol) of methyl iodide are added at 35° C. and the reaction mixture, which is now thinly liquid again, is stirred for 2 hours at 45° C. in order to complete the reaction. The salts are filtered off and the filtrate is concentrated by evaporation and the residue is chromatographed over a small column of silica gel with hexane/ethyl acetate 9:1. After concentration of the main fractions by evaporation there are obtained 4.7 g (73.4%) of the title compound (Compound No. 1.113) of the formula ##STR10## in the form of a clear colourless oil, nD21 =1.412.

Workup

  1. customAfter 30 minutes thick salt is precipitated
  2. customthe reaction
  3. filtrationThe salts are filtered off
  4. concentrationthe filtrate is concentrated by evaporation
  5. customthe residue is chromatographed over a small column of silica gel with hexane/ethyl acetate 9:1
  6. customAfter concentration of the main fractions by evaporation

Sources & evidence

ORD record
ord-0270a821cd6043cd8b75ae03062930f2
Source dataset
uspto-grants-1990_07
Patent number
US04940485

Reaction notes

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