Methyl iodide → HCID 21439984, compound

HRID 328732Notes

Reaction equation

HRID 328732 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:14][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.[CH3:20][I:21]>C(O)C>[I-:21].[CH3:20][N+:13]1[CH:12]=[CH:11][S:10][C:9]=1[NH:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:3][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 21439966Ethyl {3-chloro-4-[(1,3-thiazol-2-yl)amino]phenyl}acetate

Product 1

HCID 21439984HCID 21439984, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-[3-chloro-4-(N-thiazol-2-ylamino)phenyl]acetate (8.9 g), methyl iodide (44 ml) and ethanol (44 ml) is heated at 50°-55° C for 42 hours with stirring. The ethanol and methyl iodide are evaporated and the residue is washed with ether and kept at room temperature to give a precipitate. The precipitate is washed with ethyl acetate and cold acetone successively and recrystallized from acetone to give 3-methyl-2-[2-chloro-4-(ethoxycarbonylmethyl)anilino]-thiazolium iodide (6.6 g) melting at 147°-148° C.

Workup

  1. temperatureis heated at 50°-55° C for 42 hours
  2. customThe ethanol and methyl iodide are evaporated
  3. washthe residue is washed with ether
  4. customkept at room temperature
  5. customto give a precipitate
  6. washThe precipitate is washed with ethyl acetate and cold acetone successively
  7. customrecrystallized from acetone

Sources & evidence

ORD record
ord-f30265a530be464a98fbcf78e75a3aed
Source dataset
uspto-grants-1977_04
Patent number
US04018785

Reaction notes

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