Sodium Hydroxide → HCID 18408803, compound

HRID 993062Notes

Reaction equation

HRID 993062 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14](=[O:15])[NH:13][C:12](=[O:16])[NH:11][C:10]2=[O:17])=[CH:5][CH:4]=1.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:10](=[O:17])[NH:11][C:12](=[O:16])[NH:13][C:14]2=[O:15])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 18408750HCID 18408750, compound

Product 1

HCID 18408803HCID 18408803, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 5-(4-Methoxyphenyl)barbituric Acid (222 mg) in 5 ml of methylene chloride, kept at −5/−10° C. and under nitrogen atmosphere, is dropped a solution of boron tribromide (473 μl) in 2 ml of methylene chloride. The stirring is continued for additional 2 hours at −5° C., then the temperature is brought to room temperature and stirring is continued for further 20 hours. The reaction mixture is again cooled to 0° C. with an ice bath and it is basified to pH=9-10 by adding dropwise 5% sodium hydroxide. The aqueous phase is separated, filtered through a celite plug, cooled with ice bath and acidified to pH=1 with 37% hydrochloric acid. A white solid separates which after 1 hour is separated by filtration and dried under vacuum at 60° C. to give 215 mg of the product.

Workup

  1. custom−10° C.
  2. customis brought to room temperature
  3. waitis continued for further 20 hours
  4. customThe aqueous phase is separated
  5. filtrationfiltered through a celite plug
  6. temperaturecooled with ice bath
  7. customA white solid separates which after 1 hour is separated by filtration
  8. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-9cc3f94d773e40a88e2905c0e325218a
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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