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

HRID 1111020Notes

Reaction equation

HRID 1111020 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][CH2:20][CH3:21])=[O:17])=[O:13])=[CH:7][CH:6]=1)[CH3:4].C[O-].[Na+].[CH2:25](Br)[CH:26]=[CH:27][CH3:28]>O>[CH2:25]([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][CH2:20][CH3:21])=[O:17])=[O:13])=[CH:9][CH:10]=1)[CH3:4])[CH:26]=[CH:27][CH3:28]

Participants

5

Reactant 3

HCID 1224142-Butene, 1-bromo-HCID 10942334Sodium MethoxideHCID 86742131N-[4-(1-hydroxyiminoethyl)phenyl]-N'-(n-propoxycarbonylmethyl)urea

Product 1

HCID 54368908N-[4-(1-crotyloxyiminoethyl)phenyl]-N'-n-propoxycarbonylmethylurea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the N-[4-(1-hydroxyiminoethyl)phenyl]-N'-n-propoxycarbonylmethylurea 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'-n-propoxycarbonylmethylurea.

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-87b9dbe3c42d4db1807b5fda61acc161
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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