Propyl-2-thiourea → methyl 3-[4-phenyl-2-[N-(1-propyl)amino]-5-thiazolyl]propionate

HRID 1295260Notes

Reaction equation

HRID 1295260 reaction equation
Br[CH:2]([C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[CH2:17]([NH:20][C:21]([NH2:23])=[S:22])[CH2:18][CH3:19]>CO>[C:10]1([C:9]2[N:23]=[C:21]([NH:20][CH2:17][CH2:18][CH3:19])[S:22][C:2]=2[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 1615208Propyl-2-thioureaHCID 11066004Methyl 4-bromo-5-oxo-5-phenylpentanoate

Product 1

HCID 22930670methyl 3-[4-phenyl-2-[N-(1-propyl)amino]-5-thiazolyl]propionateYield 70.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-bromo-5-oxo-5-phenylpentanoate (5.00 g), N-propylthiourea (2.01 g) and methanol (50 ml) was refluxed for 2 hrs. The reaction solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate. The obtained solution was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give methyl 3-[4-phenyl-2-[N-(1-propyl)amino]-5-thiazolyl]propionate (3.64 g, yield 70%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 67–68° C.

Workup

  1. temperaturewas refluxed for 2 hrs
  2. customThe reaction solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe obtained solution was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fbdd9db72dfa4f60b3b7e613bf5e3f97
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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