Tetrahydrofuran → 3-(5-Methyl-2-phenyl-4-oxazolyl)propanethioamide

HRID 1294181Notes

Reaction equation

HRID 1294181 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([NH2:17])=O.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:27]2)=CC=1.O1CCCC1>C(OCC)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15](=[S:27])[NH2:17]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 87949Lawesson's reagentHCID 178613843-(5-Methyl-2-phenyl-4-oxazolyl)propanamide

Product 1

HCID 178612323-(5-Methyl-2-phenyl-4-oxazolyl)propanethioamideYield 120%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(5-methyl-2-phenyl-4-oxazolyl)propanamide (10.44 g), 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetan-2,4-disulfide (14.64 g) and tetrahydrofuran (300 mL) was stirred at room temperature for 2 hrs. To the reaction mixture was added ethyl acetate, and the mixture was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (10.7 g, 96%) of 3-(5-methyl-2-phenyl-4-oxazolyl)propanethioamide from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 167-168° C.

Workup

  1. washthe mixture was washed successively with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-9838d1754b3a4f6783e68e479b4ea510
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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