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Sodium cyanoborohydride → 5-[3-(4-Methoxyphenyl)propyl]barbituric acid

HRID 1249675
Notes
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Reaction equation

HRID 1249675 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([CH:13]2[C:18](=[O:19])[NH:17][C:16](=[O:20])[NH:15][C:14]2=[O:21])=O)=[CH:5][CH:4]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][CH:13]2[C:14](=[O:21])[NH:15][C:16](=[O:20])[NH:17][C:18]2=[O:19])=[CH:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 140406695-[3-(4-Methoxyphenyl)propionyl]barbituric acid

Product 1

HCID 140406705-[3-(4-Methoxyphenyl)propyl]barbituric acidYield 91.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 10 g of 5-[3-(4-methoxyphenyl)propionyl]barbituric acid in 100 ml of acetic acid are added portionwise 4.5 g of sodium cyanoborohydride, then the mixture is heated to 60° C. After 1 hour the reaction mixture is cooled to room temperature and poured into ice. After 30 minutes a solid is recovered by filtration, which is dried under vacuum at 50° C. to give 8.74 g of the product, m.p. 195-197° C.

Workup

  1. temperatureAfter 1 hour the reaction mixture is cooled to room temperature
  2. additionpoured into ice
  3. filtrationAfter 30 minutes a solid is recovered by filtration, which
  4. customis dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-87e0f645b23d4f3a88c7de62677b9e6f
Source dataset
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06335332B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes