Triethylamine → HCID 18756251, compound

HRID 434060Notes

Reaction equation

HRID 434060 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.[N+:18]([CH2:20][C:21]([O:23][CH3:24])=[O:22])#[C-:19].CCN(CC)CC>CN(C=O)C.C1COCC1.C(Cl)Cl>[CH3:24][O:23][C:21]([C:20]1[N:18]=[CH:19][O:6][C:4]=1[C:3]1[C:7]([F:11])=[CH:8][CH:9]=[CH:10][C:2]=1[Cl:1])=[O:22]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 679472-Chloro-6-fluorobenzoic acidHCID 547815Methyl isocyanoacetate

Product 1

HCID 18756251HCID 18756251, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-6-fluorobenzoic acid (2.14 g, 12.3 mmol), CH2Cl2 (50 ml), and DMF (2 drops) at room temperature under N2 was added oxalyl chloride (9.2 ml, 18.4 mmol) dropwise. The mixture was stirred for 3 h and the volatiles were removed under reduced pressure to give the crude acid chloride. The crude acid chloride and methyl isocyanoacetate (1.23 g, 12.3 mmol) were dissolved in THF (20 ml) at room temperature under N2 and Et3N (6.8 ml, 49.2 mmol) was added dropwise over a period of 30 minutes. The reaction was allowed to stir for 22 h followed by dilution with Et2O, extraction with H2O, 1N HCl, H2O, brine, dried (MgSO4), filtered, and concentrated. Column chromatography (silica gel, hexanes/Et2O gradient) gave 4-methoxycarbonyl-5-(2-chloro-6-fluorophenyl)oxazole (0.74 g, 24%).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customto give the crude acid chloride
  3. stirringto stir for 22 h
  4. extractionfollowed by dilution with Et2O, extraction with H2O, 1N HCl, H2O, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e7c26230571848e4a0c799777005a8f7
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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