Urea → [(4-oxo-4H-1-benzopyran-3-yl)carbonyl]urea

HRID 1578609Notes

Reaction equation

HRID 1578609 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[C:3]([C:12](Cl)=[O:13])=[CH:2]1.[NH2:15][C:16]([NH2:18])=[O:17]>C1C=CC=CC=1.S(=O)(=O)(O)O>[O:11]=[C:4]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[O:1][CH:2]=[C:3]1[C:12]([NH:15][C:16]([NH2:18])=[O:17])=[O:13]

Participants

5

Reactant 2

HCID 1176UreaHCID 15041156Chromone-3-carbonyl chloride

Product 1

HCID 21828262[(4-oxo-4H-1-benzopyran-3-yl)carbonyl]ureaYield 63%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 241BenzeneSolvent2×

Procedure

A hot solution of 10.4 g (0.05 mol) of chromone-3-carbonylchloride in 150 ml of benzene was added over two minutes to a stirred boiling mixture of 3.6 g (0.06 mol) of urea, 100 ml of benzene and two drops of conc. sulfuric acid. The mixture was stirred at reflux for 2 hrs., cooled and filtered; wt 12.3 g; mp 200°-217°. Recrystallization from dimethylformamide gave 63% yield of pure product, mp 247°-250°.

Workup

  1. temperatureat reflux for 2 hrs
  2. temperature, cooled
  3. filtrationfiltered
  4. customRecrystallization from dimethylformamide

Sources & evidence

ORD record
ord-768ea09fbe54485cbb2928b67f16621b
Source dataset
uspto-grants-1976_02
Patent number
US03937837

Reaction notes

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