2-Butene, 1-bromo- → N-[4-(1-crotyloxyiminoethyl)phenyl]-N'-ethoxycarbonylmethylurea

HRID 1111019Notes

Reaction equation

HRID 1111019 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:13])=[CH:7][CH:6]=1)[CH3:4].C[O-].[Na+].[CH2:24](Br)[CH:25]=[CH:26][CH3:27]>O>[CH2:24]([O:1][N:2]=[C:3]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([NH:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:13])=[CH:9][CH:10]=1)[CH3:4])[CH:25]=[CH:26][CH3:27]

Participants

5

Reactant 3

HCID 1224142-Butene, 1-bromo-HCID 10942334Sodium MethoxideHCID 72742601N-[4-(1-hydroxyiminoethyl)phenyl]-N'-ethoxycarbonylmethylurea

Product 1

HCID 53692223N-[4-(1-crotyloxyiminoethyl)phenyl]-N'-ethoxycarbonylmethylurea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the N-[4-(1-hydroxyiminoethyl)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 product N-[4-(1-crotyloxyiminoethyl)phenyl]-N'-ethoxycarbonylmethylurea.

Workup

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

Sources & evidence

ORD record
ord-0c2aab5e3a6b48bb9e6c65dd0b2eeb7b
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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