Acetyl chloride → 2-Methyl-4-benzoxazolecarboxamide

HRID 850053Notes

Reaction equation

HRID 850053 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C([N:7]([CH2:10][CH3:11])CC)C.C1(C)C=CC(S(O)(=O)=[O:19])=CC=1.[NH+:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=C(C)C=1>[CH3:2][C:1]1[O:3][C:25]2[C:24](=[C:11]([C:10]([NH2:7])=[O:19])[CH:28]=[CH:27][CH:26]=2)[N:23]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22033616Pyridinium.p-toluenesulfonate

Product 1

HCID 183694952-Methyl-4-benzoxazolecarboxamide

Reagents, catalysts & solvents 1

HCID 7929M-XyleneSolvent

Procedure

To a solution of the methyl (2-amino-3-hydroxy)-benzoate (3 g; 18.01 mM) in m-xylene (150 ml) was added acetyl chloride (1.518 ml; 21.6 mM). A precipitate was formed; this was left to stir for 30 minutes. On the addition of triethylamine (2.97 ml; 21.6 mM) the solution became translucent. Pyridinium-p-toluene sulphonic acid (1.2 g; 21.6 mM) was added, and the mixture refluxed for 34 hours. The solvent was removed by distillation (vacuum) to yield a brown solid which was column chromatographed (50% ethyl acetate/50% petrol 60/80) to give the desired product as a yellow solid. T.L.C. As above. 1HNMR :200 MHz; CDCl3 ; δ: 2.69(3H;s;2--CH3); 3.99(3H;s;OMe); 7.33(3H;t;H6); 7.63(1H;dd;H7); 7.94(1H;dd;H5).

Workup

  1. customA precipitate was formed
  2. waitthis was left
  3. temperaturethe mixture refluxed for 34 hours
  4. customThe solvent was removed by distillation (vacuum)
  5. customto yield a brown solid which
  6. customchromatographed (50% ethyl acetate/50% petrol 60/80)

Sources & evidence

ORD record
ord-062e953fb8ee4fb1b549a0cf3df4bd6d
Source dataset
uspto-grants-2000_01
Patent number
US06015827

Reaction notes

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