Methyl iodide → HCID 53686750, compound

HRID 2231153Notes

Reaction equation

HRID 2231153 reaction equation
[CH3:1][N:2]([CH3:21])[C:3](=[O:20])[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:5]([OH:14])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13].[C:22]([O-])([O-])=O.[K+].[K+].CI>CCC(C)=O.CCOCC.O.C([O-])(O)=O.[Na+]>[CH3:21][N:2]([CH3:1])[C:3](=[O:20])[C:4]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:5]([O:14][CH3:22])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13]

Participants

8

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 67899397HCID 67899397, compound

Product 1

HCID 53686750HCID 53686750, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6569Methyl Ethyl KetoneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 5.0 g (0.015 mole) of N,N-dimethylalpha-ethoxycarbonyl-beta-hydroxy-2,4-dichlorocinnamamide and 4.14 g (0.03 mole) anhydrous powdered K2CO3 in 100 ml MEK was heated to reflux for 30 minutes then cooled to room temperature. To the slurry was added 2.44 g (0.0165 mole) CH3I dropwise. The reaction mixture was stirred at room temperature an additional 30 minutes then heated to reflux for 2 hours and then cooled again to room temperature. The reaction was worked-up by diluting with 200 ml ether washing successively with water (2×100 ml) and 10% NaHCO3 (2×100 ml) and then drying the organic phase over anhydrous MgSO4, filtering, and stripping off the ether to yield 5.2 g of a semi-solid. The semi-solid was crystallized from ether/hexanes to yield 4.0 g of the product, mp 88°-92°.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. temperaturethen heated
  4. temperatureto reflux for 2 hours
  5. temperaturecooled again to room temperature
  6. dry with materialdrying the organic phase over anhydrous MgSO4
  7. filtrationfiltering

Sources & evidence

ORD record
ord-6231658c5d374209a3f6850603ff7cb0
Source dataset
uspto-grants-1988_11
Patent number
US04781750

Reaction notes

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