2-Butene, 1-bromo- → Ethyl hydantoate

HRID 1111005Notes

Reaction equation

HRID 1111005 reaction equation
ON=CC1C=CC([NH:10][C:11]([NH:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:12])=CC=1.C[O-].[Na+].C(Br)C=CC>O>[CH2:18]([O:17][C:15]([CH2:14][NH:13][C:11](=[O:12])[NH2:10])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 1224142-Butene, 1-bromo-HCID 10942334Sodium MethoxideHCID 867443964-(hydroxyiminomethyl)phenyl-N'-ethoxycarbonylmethylurea

Product 1

HCID 222535Ethyl hydantoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-[4-(hydroxyiminomethyl)phenyl]-N'-ethoxycarbonylmethylurea in 25% methanolic sodium methoxide (1.0 equivalent) is treated at room temperature with 1.1 equivalent of crotyl bromide. The reaction mixture is stirred until the temperature falls to about 20° C. The reaction mixture is then poured into cold water and extracted with diethyl ether The ether solution is dried over MgSO4 and filtered, and the solvent is removed by rotary evaporator to yield the corresponding N-[4-crotyloxyiminomethyl)phenyl]-N'-ethoxycarbonylmethylurea.

Workup

  1. customfalls to about 20° C
  2. extractionextracted with diethyl ether The ether solution
  3. dry with materialis dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is removed by rotary evaporator

Sources & evidence

ORD record
ord-2f143d14ef1843ab9fe27bc5bb02b4dc
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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