Nitrogen → HCID 67957879, compound

HRID 82848Notes

Reaction equation

HRID 82848 reaction equation
N#N.[Cl:3][CH2:4][C:5]1[O:6][CH:7]=[C:8]([CH2:10][OH:11])[N:9]=1.[CH2:12](I)[CH3:13]>C(Cl)Cl>[Cl:3][CH2:4][C:5]1[O:6][CH:7]=[C:8]([CH2:10][O:11][CH2:12][CH3:13])[N:9]=1

Participants

5

Reactant 3

HCID 947NitrogenHCID 6340IodoethaneHCID 67958068(2-(Chloromethyl)oxazol-4-yl)methanol

Product 1

HCID 67957879HCID 67957879, 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 (2-(chloromethyl)oxazol-4-yl)methanol (500 mg, 3.39 mmol) in CH2Cl2 (2.0 mL) was treated with EtI (0.28 mL, 3.39 mmol) followed by Ag2O (1.18 g, 5.08 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 (7:3 hept-EA) gave the title compound as a yellow oil: TLC: rf (7:3 hept-EA)=0.29. LC-MS-conditions 07: tR=0.62 min, [M+H]+=176.26.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under reduced pressure
  3. customPurification of the residue by FC (7:3 hept-EA)

Sources & evidence

ORD record
ord-5ddf421da2d54c7cb5d9b0321fe2070e
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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