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

HRID 1414542Notes

Reaction equation

HRID 1414542 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-toluene sulfonic acid. The solution is heated at reflux under nitrogen for four 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-d2e926817b9045e19496deef48436701
Source dataset
uspto-grants-1977_01
Patent number
US04001425

Reaction notes

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