Iodoethane → 4-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-ethoxycarbonyl-2-methoxyphenyl)-N-propylamino]thiazole hydrochloride

HRID 1698868Notes

Reaction equation

HRID 1698868 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]([C:26]([OH:28])=[O:27])[CH:23]=[CH:22][C:21]=2[O:29][CH3:30])[CH2:17][CH2:18][CH3:19])[S:13][C:14]=1[CH3:15].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:37](I)[CH3:38]>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]([C:26]([O:28][CH2:37][CH3:38])=[O:27])[CH:23]=[CH:22][C:21]=2[O:29][CH3:30])[CH2:17][CH2:18][CH3:19])[S:13][C:14]=1[CH3:15]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 183222624-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-carboxy-2-methoxyphenyl)-N-propylamino]thiazole

Product 1

HCID 183222474-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-ethoxycarbonyl-2-methoxyphenyl)-N-propylamino]thiazole hydrochloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1 g of 4-(2-chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-carboxy-2methoxyphenyl)-N-propylamino]thiazole (EXAMPLE 3) is dissolved at room temperature and under argon in 3 ml of dimethylformamide and then 0.66 g of Cs2CO3 and 0.5 ml of ethyl iodide are added. The reaction mixture is stirred for one hour and then diluted with ethyl acetate. It is washed with water, dried over sodium sulphate and evaporated to dryness. The residue is purified by chromatography on a silica gel column eluted with a cyclohexane/ethyl acetate 5/1 (v/v) mixture. The expected product is obtained in the form of a colourless oil.

Workup

  1. washIt is washed with water
  2. dry with materialdried over sodium sulphate
  3. customevaporated to dryness
  4. customThe residue is purified by chromatography on a silica gel column
  5. washeluted with a cyclohexane/ethyl acetate 5/1 (v/v) mixture

Sources & evidence

ORD record
ord-37ee00064d1e4c8ab4b2bc1d16616d30
Source dataset
uspto-grants-2002_02
Patent number
US06344470B1

Reaction notes

Loading…