4-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-carboxy-2-methoxyphenyl)-N-propylamino]thiazole → 4-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-hydroxymethyl-2-methoxyphenyl)-N-propylamino]thiazole

HRID 1698870Notes

Reaction equation

HRID 1698870 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](O)=[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].[H-].[Al+3].[Li+].[H-].[H-].[H-].ClCCl.C(OCC)(=O)C>O1CCCC1>[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:29][CH3:30])[CH2:17][CH2:18][CH3:19])[S:13][C:14]=1[CH3:15]

Participants

5

Reactant 3

HCID 183222624-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-carboxy-2-methoxyphenyl)-N-propylamino]thiazoleHCID 21226138Dichloromethane ethylacetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 183222484-(2-Chloro-4-methoxyphenyl)-5-methyl-2-[N-(5-hydroxymethyl-2-methoxyphenyl)-N-propylamino]thiazoleYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At 0° C., under an inert atmosphere, 1.5 g of 4-(2-chloro-4-methoxyphenyl)-5methyl-2-[N-(5-carboxy-2-methoxyphenyl)-N-propylamino]thiazole are dissolved in 11 ml of tetrahydrofuran. 5 ml of a 1 M solution of lithium aluminium hydride in tetrahydrofuran are added slowly so that the temperature of the mixture does not exceed 10° C. After 2 hours at room temperature, the reaction mixture is cooled with the aid of an ice bath and then hydrolyzed slowly. The crude material is alkalanized before being filtered over sodium sulphate. After evaporation under vacuum, the product is obtained by purification on a silica gel; eluent: dichloro-methane/ethyl acetate 95/5 (v/v); yield=87%. The expected product is in the form of a powder; m.p.=115° C.

Workup

  1. customdoes not exceed 10° C
  2. temperaturethe reaction mixture is cooled with the aid of an ice bath
  3. filtrationbefore being filtered over sodium sulphate
  4. customAfter evaporation under vacuum
  5. customthe product is obtained by purification on a silica gel

Sources & evidence

ORD record
ord-655683a367c84e6ea45ca2a7e573eb76
Source dataset
uspto-grants-2002_02
Patent number
US06344470B1

Reaction notes

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