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Allyl bromide → N-[4-(1-allyloxyiminoethyl)phenyl]-N'-isopropoxycarbonylmethylurea

HRID 1111021
Notes
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Reaction equation

HRID 1111021 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][CH:19]([CH3:21])[CH3:20])=[O:17])=[O:13])=[CH:7][CH:6]=1)[CH3:4].C[O-].[Na+].[CH2:25](Br)[CH:26]=[CH2:27]>O>[CH2:27]([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][CH:19]([CH3:21])[CH3:20])=[O:17])=[O:13])=[CH:9][CH:10]=1)[CH3:4])[CH:26]=[CH2:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10942334Sodium MethoxideHCID 72742602N-[4-(1-hydroxyiminoethyl)phenyl]-N'-isopropoxycarbonylmethylurea

Product 1

HCID 54128761N-[4-(1-allyloxyiminoethyl)phenyl]-N'-isopropoxycarbonylmethylurea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the N-[4-(1-hydroxyiminoethyl)phenyl]-N'-isopropoxycarbonylmethylurea in 25% methanolic sodium methoxide (1.0 equivalent) is treated at room temperature with 1.1 equivalent of allyl 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-allyloxyiminoethyl)phenyl]-N'-isopropoxycarbonylmethylurea.

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-ca254232c13e4cf6a5976595cec640d0
Source dataset
uspto-grants-1990_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04977272

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes