Methanol → 6-[(3-Phenylpropyl)amino]-1,3-benzoxazol-2(3H)-one

HRID 1762819Notes

Reaction equation

HRID 1762819 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[C:12]1([CH2:18][CH2:19][CH:20]=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CO.[BH4-].[Na+]>C1C=CC=CC=1>[C:12]1([CH2:18][CH2:19][CH2:20][NH:1][C:2]2[CH:11]=[CH:10][C:5]3[NH:6][C:7](=[O:9])[O:8][C:4]=3[CH:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7707BenzenepropanalHCID 8269896-amino-1,3-benzoxazol-2(3H)-oneHCID 4311764Sodium borohydride

Product 1

HCID 143280786-[(3-Phenylpropyl)amino]-1,3-benzoxazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 6-amino-2-benzoxazolone (6.00 g) and molecular sieves 4A (10.0 g) in dry benzene (100 ml) was added 3-phenylpropanal (5.25 ml), and then the mixture was stirred at room temperature for 1 hour. Methanol (150 ml) was combined with this and sodium borohydride (1.50 g) was added in portions at room temperature. The reaction mixture was filtered, the filtrate was concentrated and 5% sodium bicarbonate was added. The organic material was extracted with dichloromethane. The dichloromethane phase was separated, washed with brine. Drying and removal of solvent under reduced pressure gave a crude product which was crystallized from hot ethanol to afford 7.07 g of the title compound: mp 129°-130° C.

Workup

  1. additionwas added in portions at room temperature
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. addition5% sodium bicarbonate was added
  5. extractionThe organic material was extracted with dichloromethane
  6. customThe dichloromethane phase was separated
  7. washwashed with brine
  8. customDrying
  9. customremoval of solvent under reduced pressure
  10. customgave a crude product which
  11. customwas crystallized from hot ethanol

Sources & evidence

ORD record
ord-872f4d39c946407f88eda255ad017238
Source dataset
uspto-grants-1989_05
Patent number
US04835166

Reaction notes

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