Potassium Carbonate → HCID 59567847, compound

HRID 2088492Notes

Reaction equation

HRID 2088492 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[O:9])[S:5][C:6]=1[CH3:7].CC1C=CC(S([CH2:20][N:21]=[CH2:22])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][CH:22]=[N:21][CH:20]=2)[S:5][C:6]=1[CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 562852HCID 562852, compoundHCID 155382124-Bromo-5-methylthiophene-2-carbaldehyde

Product 1

HCID 59567847HCID 59567847, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-bromo-5-methylthiophene-2-carbaldehyde (A, 10.5 mmol) and p-tosylmethyl isocyanide (11 mmol) in methanol (80 mL) was added potassium carbonate (13 mmol) and the mixture was heated to 80° C. for 1 h. The solvent was removed in vacuo and diluted in DCM (100 mL) and water (100 mL). The organic layer dried, concentrated and purified by flash chromatography to give 5-(4-bromo-5-methylthiophen-2-yl)oxazole (B, 1.83 g) as yellowish solids.

Workup

  1. customThe solvent was removed in vacuo
  2. additiondiluted in DCM (100 mL)
  3. customThe organic layer dried
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-17245e31cc4a45dc96ca31dae92db35f
Source dataset
uspto-grants-2013_05
Patent number
US08435996B2

Reaction notes

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