Water → 1-(1,1-Dimethylbutyl)-3-(2,5-dihydro-5-oxo-3-furyl)urea

HRID 918079Notes

Reaction equation

HRID 918079 reaction equation
C[O:2][C:3](=[O:9])[CH2:4][C:5]([CH2:7]Br)=O.[CH3:10][C:11]([NH:16][C:17]([NH2:19])=[O:18])([CH3:15])[CH2:12][CH2:13][CH3:14].O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:10][C:11]([NH:16][C:17]([NH:19][C:5]1[CH2:7][O:2][C:3](=[O:9])[CH:4]=1)=[O:18])([CH3:15])[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 962WaterHCID 295655Methyl 4-bromo-3-oxobutanoateHCID 233418801,1-Dimethylbutylurea

Product 1

HCID 214878901-(1,1-Dimethylbutyl)-3-(2,5-dihydro-5-oxo-3-furyl)ureaYield 8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 22 g of methyl-4-bromoacetoacetate in 200 ml benzene is added 14.4 g of 1,1-dimethylbutylurea and 100 mg of p-toluenesulfonic acid. The solution is heated at reflux under nitrogen for 4 hours with water removal. At the end of this period the solution is cooled and concentrated. The residual material is chromatographed on 400 g of silicic acid. Elution with a solution of benzene (60%), ethyl acetate (30%) and methanol (10%) gives crystalline material. Recrystallization of this material from ethyl acetate gives 1.8 g of 1-(1,1-dimethylbutyl)-3-(2,5-dihydro-5-oxo-3-furyl)urea, m.p. 130°-132°C.

Workup

  1. temperatureThe solution is heated
  2. temperatureAt the end of this period the solution is cooled
  3. concentrationconcentrated
  4. customThe residual material is chromatographed on 400 g of silicic acid
  5. washElution with a solution of benzene (60%), ethyl acetate (30%) and methanol (10%)
  6. customgives crystalline material
  7. customRecrystallization of this material from ethyl acetate

Sources & evidence

ORD record
ord-d9640d1cef3b4732a6f9d9e67cf51a7e
Source dataset
uspto-grants-1976_07
Patent number
US03969370

Reaction notes

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