Nitrogen → HCID 57960183, compound

HRID 82843Notes

Reaction equation

HRID 82843 reaction equation
N#N.[OH:3][CH2:4][C:5]1[O:6][CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=1.[CH3:14]I>C(Cl)Cl>[CH3:14][O:3][CH2:4][C:5]1[O:6][CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 6328Methyl iodideHCID 67281821HCID 67281821, compound

Product 1

HCID 57960183HCID 57960183, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of methyl 2-(hydroxymethyl)oxazole-4-carboxylate (231 mg, 1.47 mmol) in CH2Cl2 (0.9 mL) was treated with MeI (0.11 mL, 1.76 mmol) followed by Ag2O (511 mg, 2.21 mmol) and the resulting mixture (protected from light) was stirred overnight at 40° C. The reaction mixture was filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (1:1 hept-EA) gave the title compound as a colorless oil: TLC: rf (1:1 hept-EA)=0.33. LC-MS-conditions 07: tR=0.49 min, [M+H]+=172.20.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under reduced pressure
  3. customPurification of the residue by FC (1:1 hept-EA)

Sources & evidence

ORD record
ord-4bb216c17d44415d9ff82aa4f3b5dbd9
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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