Methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate → Methyl 4-[4-[(acetylsulfanyl)methyl]-5-methyl-1,3-oxazol-2-yl]benzoate

HRID 931486Notes

Reaction equation

HRID 931486 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[C:19](=[S:22])([O-:21])[CH3:20].[K+]>CC(C)=O.[I-].[K+]>[C:19]([S:22][CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8])(=[O:21])[CH3:20]

Participants

5

Reactant 2

HCID 23076573Methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoateHCID 23670855Potassium ethanethioate

Product 1

HCID 86709133Methyl 4-[4-[(acetylsulfanyl)methyl]-5-methyl-1,3-oxazol-2-yl]benzoateYield 91.4%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

A solution of methyl 4-[4-(chloromethyl)-5-methyl-1,3-oxazol-2-yl]benzoate (10 g, 37.64 mmol, 1.00 equiv), potassium ethanethioate (5 g, 43.78 mmol, 1.16 equiv) and potassium iodide (300 mg, 1.81 mmol, 0.05 equiv) in acetone (160 mL) was stirred at 35° C. under nitrogen for 30 min. The product was precipitated by the addition of 250 mL water. The precipitate was collected by filtration, washed with water and dried in a vacuum oven to give 10.5 g (91%) of methyl 4-[4-[(acetylsulfanyl)methyl]-5-methyl-1,3-oxazol-2-yl]benzoate as a white solid.

Workup

  1. customThe product was precipitated by the addition of 250 mL water
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-2a7d4695556944a2939e03b6748bf2dd
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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