Triethylamine → 5-(3,4-Dichloro-phenyl)-oxazole-4-carboxylic acid methyl ester

HRID 2265208Notes

Reaction equation

HRID 2265208 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[C-:2].[Cl:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[Cl:18])[C:12](Cl)=[O:13].CCN(CC)CC>C1COCC1>[CH3:7][O:6][C:4]([C:3]1[N:1]=[CH:2][O:13][C:12]=1[C:11]1[CH:15]=[CH:16][C:17]([Cl:18])=[C:9]([Cl:8])[CH:10]=1)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 547815Methyl isocyanoacetate

Product 1

HCID 687696805-(3,4-Dichloro-phenyl)-oxazole-4-carboxylic acid methyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl isocyanoacetate (5.0 g, 50.0 mmol), 3,4-dichlorobenzoyl chloride (10.6 g, 50.0 mmol), and Et3N (20.9 mL, 150 mmol) was stirred in THF (20 mL) for 48 h at rt. The solution was concentrated, diluted with EtOAc, washed with water, dried (MgSO4), and concentrated to afford a solid. The solid was washed with hexanes and collected by filtration to provide 8.7 g (64%) of the desired product. HPLC: RT=9.68 min. MS (ESI+): mass calcd. for C11H7Cl2NO3, 270.98; m/z found, 272/274 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.29 (d, J=2.1, 1H), 8.03 (dd, J=8.5, 2.1, 1H), 7.94 (s, 1H), 7.56 (d, J=8.5, 1H), 3.98 (s, 3H).

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto afford a solid
  7. washThe solid was washed with hexanes
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-21c948592e574111820c93c229e3dd1b
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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