Methanol → 4-(2,4-Dichlorophenyl)-5-methyl-2-{N-[alpha-cyclopropyl-4-(methoxycarbonyl)benzyl]-N-propylamino}thiazole

HRID 399630Notes

Reaction equation

HRID 399630 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[C:13]1[N:14]=[C:15]([N:19]([CH:23]([CH2:33][CH2:34][CH3:35])[C:24]2[CH:29]=[CH:28][C:27]([C:30]([OH:32])=[O:31])=[CH:26][CH:25]=2)[CH2:20][CH2:21][CH3:22])[S:16][C:17]=1[CH3:18].[CH3:36]O>>[Cl:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[C:13]1[N:14]=[C:15]([N:19]([CH:23]([CH:33]2[CH2:35][CH2:34]2)[C:24]2[CH:25]=[CH:26][C:27]([C:30]([O:32][CH3:36])=[O:31])=[CH:28][CH:29]=2)[CH2:20][CH2:21][CH3:22])[S:16][C:17]=1[CH3:18]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 18967756HCID 18967756, compound

Product 1

HCID 152916104-(2,4-Dichlorophenyl)-5-methyl-2-{N-[alpha-cyclopropyl-4-(methoxycarbonyl)benzyl]-N-propylamino}thiazoleYield 79%

Conditions

Temperature
40 °C

Procedure

200 mg of thionyl chloride are added to 390 mg of the compound of Example 1 dissolved in 100 ml of anhydrous methanol and the solution is then maintained at 40° C. under argon for 16 hours. After evaporation under vacuum, the residue is purified on a column of silica, using a mixture of cyclohexane and ethyl acetate (10:1 v/v) as eluent. 4-(2,4-Dichlorophenyl)-5-methyl-2-{N-[α-cyclopropyl-4-(methoxycarbonyl)benzyl]-N-propylamino}thiazole is thus obtained.

Workup

  1. customAfter evaporation under vacuum
  2. customthe residue is purified on a column of silica
  3. additiona mixture of cyclohexane and ethyl acetate (10:1 v/v) as eluent

Sources & evidence

ORD record
ord-f5e296ac2120448a88b724ce8a11b3ad
Source dataset
uspto-grants-1998_10
Patent number
US05821255

Reaction notes

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