Triethylamine → 4-Oxazolecarboxylic acid, 5-(4-chlorophenyl)-, methyl ester

HRID 2092243Notes

Reaction equation

HRID 2092243 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[N:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:12]=O.C(N(CC)CC)C>C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:7][CH:12]=[N:11][C:14]=2[C:15]([O:17][CH3:18])=[O:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 2769479Methyl 2-isocyanatoacetate

Product 1

HCID 118463424-Oxazolecarboxylic acid, 5-(4-chlorophenyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.40 g (8.00 mmol) of 4-chlorobenzoyl chloride, 1.00 g (10.09 mmol) of methyl isocyanatoacetate and 5.9 ml (42.39 mmol) of triethylamine are dissolved in 15 ml of dry THF and stirred at RT for 48 h. The solvent is then removed on a rotary evaporator. The residue is taken up in 20 ml of ethyl acetate and washed once with 5 ml of water. The organic phase is dried over magnesium sulfate and the solvent is removed on a rotary evaporator. The residue is suspended in 10 ml of cyclohexane and filtered off. It is then recrystallized from about 10 ml of methanol. This gives needle-shaped crystals which are dried in a drying cabinet at 50° C. A further product fraction is obtained by reprecipitation after recrystallization.

Workup

  1. customThe solvent is then removed on a rotary evaporator
  2. washwashed once with 5 ml of water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customthe solvent is removed on a rotary evaporator
  5. filtrationfiltered off
  6. customIt is then recrystallized from about 10 ml of methanol
  7. customThis gives needle-shaped crystals which are dried in a drying cabinet at 50° C
  8. customA further product fraction is obtained by reprecipitation
  9. customafter recrystallization

Sources & evidence

ORD record
ord-1115645405724ff78f54f0c1c34196a0
Source dataset
uspto-grants-2013_05
Patent number
US08440700B2

Reaction notes

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