Hydrochloric Acid → HCID 18408754, compound

HRID 1872565Notes

Reaction equation

HRID 1872565 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10][C:9]2=[O:16])=[CH:4][CH:3]=1.[C:17]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])([CH3:19])[CH3:18].N1C=CN=C1.Cl>>[C:17]([Si:21]([CH3:23])([CH3:22])[O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:9](=[O:16])[NH:10][C:11](=[O:15])[NH:12][C:13]2=[O:14])=[CH:6][CH:7]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 18408803HCID 18408803, compound

Product 1

HCID 18408754HCID 18408754, compoundYield 75.7%

Conditions

Temperature
55 °C

Procedure

To a solution of 5-(4-hydroxyphenyl)barbituric acid (1.9 g) and tertbutyl dimethylsilyl chloride (4.68 g) in 20 ml of anhydrous dimethylformlamde are added 4.4 g of imidazole and the mixture is heated to 55° C. for 5 hours. The temperature is then brought to room temperature and the reaction mixture is poured into 1 N hydrochloric acid and extracted twice with ethyl acetate. The pooled organic extracts are washed with water and dried over sodium sulfate. By concentration of the solution a white solid separates, which is kept at 0° C. overnight, then it is filtered to give 2.185 g of the product

Workup

  1. customis then brought to room temperature
  2. extractionextracted twice with ethyl acetate
  3. washThe pooled organic extracts are washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationit is filtered

Sources & evidence

ORD record
ord-75d9c05d07534911a1b7eff4c8818047
Source dataset
uspto-grants-2000_08
Patent number
US06110924

Reaction notes

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