Barbituric Acid → HCID 15292573, compound

HRID 1420090Notes

Reaction equation

HRID 1420090 reaction equation
[NH:1]1[C:8](=[O:9])[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[OH:10][C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[C:18]=1[OH:19])[CH:14]=O.S(Cl)(Cl)=O>CC(O)C>[OH:10][C:11]1[CH:12]=[C:13]([CH:14]=[C:7]2[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][C:8]2=[O:9])[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[C:18]=1[OH:19]

Participants

5

Reactant 3

HCID 6211Barbituric AcidHCID 24386Thionyl ChlorideHCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

Product 1

HCID 15292573HCID 15292573, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution containing 1.28 g (0.01 mol) of barbituric acid and 1.83 g (0.01 mol) of 3,4-dihydroxy-5-nitrobenzaldehyde in 20 ml of 2-propanol was gradually added 5.0 ml of thionyl chloride. The mixture was stirred for 100 h at room temperature. The product was filtered, washed with 2-propanol and recrystallized from acetic acid. Yield 1.28 g (44%), mp 269°-272° C.

Workup

  1. filtrationThe product was filtered
  2. washwashed with 2-propanol
  3. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-4018ac783685400c978b1c613226b265
Source dataset
uspto-grants-1999_03
Patent number
US05889037

Reaction notes

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