Dichloromethane → 4-Methyl-3H-benzooxazol-2-one

HRID 1777736Notes

Reaction equation

HRID 1777736 reaction equation
[OH:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11].C(Cl)Cl>C1COCC1>[CH3:9][C:5]1[C:3]2[NH:4][C:10](=[O:11])[O:1][C:2]=2[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 30141382-Amino-m-cresol

Product 1

HCID 127093364-Methyl-3H-benzooxazol-2-oneYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-hydroxy-6-methylaniline (583 mg) in THF (8 mL) was added 1,1′-carbonyldiimidazole (1.14 g). The reaction mixture was stirred at 70° C. for 20 h. After cooling down, DCM was added and the mixture was washed three times with 2N NaOH. The aq. phases were combined, cooled down to 0° C. and the pH was brought to 6 by addition of 2N HCl. The suspension was filtered, the resulting powder was washed with cold water and dried in high vacuo to afford 587 mg of beige solid. LC-MS (B): tR=0.64 min. 1H-NMR (DMSO-d6): 11.7 (s, NH); 7.09 (m, 1H); 6.97 (m, 2H); 2.29 (s, 3H).

Workup

  1. temperatureAfter cooling down
  2. washthe mixture was washed three times with 2N NaOH
  3. temperaturecooled down to 0° C.
  4. additionthe pH was brought to 6 by addition of 2N HCl
  5. filtrationThe suspension was filtered
  6. washthe resulting powder was washed with cold water
  7. customdried in high vacuo

Sources & evidence

ORD record
ord-7a05325f2f1940af9642d4d4db188386
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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