Methyl iodide → 4-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(2-methoxy-5-methoxymethylphenyl)-N-propylamino]thiazole hydrochloride

HRID 1698871Notes

Reaction equation

HRID 1698871 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:11]=[C:12]([N:16]([C:20]2[CH:25]=[C:24]([CH2:26][OH:27])[CH:23]=[CH:22][C:21]=2[O:28][CH3:29])[CH2:17][CH2:18][CH3:19])[S:13][C:14]=1[CH3:15].[H-].[Na+].[CH3:32]I>CN(C)C=O.C(OCC)(=O)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[N:11]=[C:12]([N:16]([C:20]2[CH:25]=[C:24]([CH2:26][O:27][CH3:32])[CH:23]=[CH:22][C:21]=2[O:28][CH3:29])[CH2:17][CH2:18][CH3:19])[S:13][C:14]=1[CH3:15]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 183222484-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-hydroxymethyl-2-methoxyphenyl)-N-propylamino]thiazole

Product 1

HCID 183222644-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(2-methoxy-5-methoxymethylphenyl)-N-propylamino]thiazole hydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

At 0° C., under an inert atmosphere, 320 mg of 4-(2-chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-hydroxymethyl-2-methoxyphenyl)-N-propylamino]thiazole are dissolved in 0.7 ml of dimethylformamide. 70 mg of sodium hydride (50% in oil) are added. After 5 minutes, 0.24 ml of methyl iodide is added. After 12 hours at room temperature, the reaction mixture is diluted with ethyl acetate and then hydrolyzed. The organic phase is washed several times with water before being dried over sodium sulphate. After purification on a silica gel; the expected product is dissolved in dichloromethane. A 0.1 N solution of hydrochloric acid in isopropanol is then added. After evaporation under vacuum, the expected product is obtained in hydrochloride form; m.p.=71° C.

Workup

  1. waitAfter 12 hours at room temperature
  2. washThe organic phase is washed several times with water
  3. dry with materialbefore being dried over sodium sulphate
  4. customAfter purification on a silica gel
  5. dissolutionthe expected product is dissolved in dichloromethane
  6. additionA 0.1 N solution of hydrochloric acid in isopropanol is then added
  7. customAfter evaporation under vacuum

Sources & evidence

ORD record
ord-1079f1e2cc3b41d8889f99e8fffd3c48
Source dataset
uspto-grants-2002_02
Patent number
US06344470B1

Reaction notes

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