Methyl iodide → HCID 21440040, compound

HRID 328730Notes

Reaction equation

HRID 328730 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]1[S:10][CH:11]=[CH:12][N:13]=1.[CH3:21]I>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[CH:6][C:7]=1[N:8]=[C:9]1[N:13]([CH3:21])[CH:12]=[CH:11][S:10]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 21439952HCID 21439952, compound

Product 1

HCID 21440040HCID 21440040, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 2-[3-chloro-4-(N-thiazol-2-ylamino)phenyl]propionate (3.8 g), methyl iodide (11.4 ml) and ethanol (11.4 ml) is heated at 100° C for 6 hours in a sealed tube. The ethanol and methyl iodide are evaporated. The residue is washed with benzene and dissolved in methylene chloride. The solution is washed with 20 % aqueous potassium carbonate solution and evaporated to remove methylene chloride. The residue is treated in the same manner as in Example 1 to give ethyl 2-[3-chloro-4-(3-methyl-4-thiazolin-2-ylideneamino)phenyl]propionate (2.45 g). (Yield 62 %).

Workup

  1. customThe ethanol and methyl iodide are evaporated
  2. washThe residue is washed with benzene
  3. dissolutiondissolved in methylene chloride
  4. washThe solution is washed with 20 % aqueous potassium carbonate solution
  5. customevaporated
  6. customto remove methylene chloride
  7. additionThe residue is treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-a790a6769a53468991b30d9f42cef3ea
Source dataset
uspto-grants-1977_04
Patent number
US04018785

Reaction notes

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