Aniline → 5-(Phenylcarbamoyl)-2-methylbenzoxazole

HRID 369563Notes

Reaction equation

HRID 369563 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([CH3:12])=[N:9][C:8]=2[CH:13]=1)([OH:3])=O.P(Cl)(Cl)(Cl)=O.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[C:20]1([NH:19][C:1]([C:4]2[CH:5]=[CH:6][C:7]3[O:11][C:10]([CH3:12])=[N:9][C:8]=3[CH:13]=2)=[O:3])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 24813Phosphorus oxychlorideHCID 232822842-Methyl-1,3-benzoxazole-5-carboxylic acid

Product 1

HCID 232822835-(Phenylcarbamoyl)-2-methylbenzoxazoleYield 594.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

5-Carboxy-2-methylbenzoxazole (2.0 g, 1.1 mmol) and phosphorous oxychloride (10 mL) were combined and heated at 100° C. for 1 hr. The reaction mixture was evaporated and the resulting oil was dissolved in 20 mL of acetonitrile and poured into a mixture of ice and water. The solid formed was collected, dissolved in 40 mL of acetonitrile and combined with aniline (2.0 g, 2.2 mmol). After stirring 45 min. the reaction mixture was poured into 500 mL of a mixture of ice and water. The resulting solid was collected and dried affording 1.65 g (58% yield) of 5-(Phenylcarbamoyl)-2-methylbenzoxazole, mp 137.5-139.0° C. Anal. Calcd for C15H12N2O2 : C, 71.42; H, 4.79; N, 11.10. Found: C, 71.16; H, 4.83; N, 10.96.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe resulting oil was dissolved in 20 mL of acetonitrile
  3. additionpoured into a mixture of ice and water
  4. customThe solid formed
  5. customwas collected
  6. dissolutiondissolved in 40 mL of acetonitrile
  7. customThe resulting solid was collected
  8. customdried

Sources & evidence

ORD record
ord-8cbef3c805be43888c7c3393fb06f015
Source dataset
uspto-grants-2000_10
Patent number
US06140036

Reaction notes

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