Nitrogen → HCID 67281821, compound

HRID 82842Notes

Reaction equation

HRID 82842 reaction equation
N#N.[Na].C([O:7][CH2:8][C:9]1[O:10][CH:11]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[N:13]=1)(=O)C.[NH4+].[Cl-]>CO>[OH:7][CH2:8][C:9]1[O:10][CH:11]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[N:13]=1

Participants

6

Reactant 4

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 66660861Methyl 2-(acetoxymethyl)oxazole-4-carboxylate

Product 1

HCID 67281821HCID 67281821, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), sodium (1.32 g, 57.42 mmol) was added portionwise to MeOH (145 mL). Methyl 2-(acetoxymethyl)oxazole-4-carboxylate (23.30 g, 116.99 mmol) was then added and the reaction mixture was stirred for 1 h at rt. Sat. aq. NH4Cl (760 mL) was then added and the mixture was extracted with EA (2×760 mL). The combined org. layers were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a white solid: TLC: rf (1:9 hept-EA)=0.33. LC-MS-conditions 06: tR=0.31 min, [M+H]+=158.15.

Workup

  1. extractionthe mixture was extracted with EA (2×760 mL)
  2. dry with materiallayers were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-ef52a1494ad64d6a97705e1bc8327552
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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