Methyl iodide → HCID 131721151, compound

HRID 1418040Notes

Reaction equation

HRID 1418040 reaction equation
[H-].[Na+].[CH3:3]I.[Cl:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[C:14]1[N:15]=[C:16]([N:20]([C:24]2[CH:25]=[C:26]3[C:30](=[CH:31][CH:32]=2)[NH:29][CH:28]=[CH:27]3)[CH2:21][CH2:22][CH3:23])[S:17][C:18]=1[CH3:19]>CN(C)C=O>[Cl:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=1[C:14]1[N:15]=[C:16]([N:20]([C:24]2[CH:25]=[C:26]3[C:30](=[CH:31][CH:32]=2)[N:29]([CH3:3])[CH:28]=[CH:27]3)[CH2:21][CH2:22][CH3:23])[S:17][C:18]=1[CH3:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67620600HCID 67620600, compound

Product 1

HCID 131721151HCID 131721151, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.045 g of 55% sodium hydride in oil and then 0.12 ml of methyl iodide are added, at 4° C., to 0.39 g of 4-(2-chloro-4-methoxyphenyl)-5-methyl-2-[N-(indol-5-yl)-N-propylamino]thiazole obtained above (EXAMPLE 7) in solution in 5 ml of dimethylformamide. After stirring for 5 hours at room temperature, the reaction mixture is poured into ice-cold water. The mixture is extracted with ethyl acetate and the organic phase is washed a number of times with water, dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on a column of silica gel eluted with a 9/1 (v/v) cyclohexane/ethyl acetate mixture. The expected product is isolated in the form of a white solid; M.p.=146° C. 1H NMR (CDCl3): 0.92 (m, 3H), 1.58-1.73 (m, 2H), 2.01 (s, 3H), 3.81-4.0 (m, 8H), 6.51 (d, J=2.8, 1H), 6.85 (dd, J=2.2, 8.4, 1H), 6.99 (d, J=2.0, 1H), 7.09-7.20 (m, 2H), 7.35-7.40 (m, 2H), 7.62 (s, 1H).

Workup

  1. additionthe reaction mixture is poured into ice-cold water
  2. extractionThe mixture is extracted with ethyl acetate
  3. washthe organic phase is washed a number of times with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated to dryness
  6. customThe residue is purified by chromatography on a column of silica gel
  7. washeluted with a 9/1 (v/v) cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-1b1bc6185146466abaa742ba1d39d628
Source dataset
uspto-grants-1999_03
Patent number
US05880135

Reaction notes

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