Allyl bromide → N'-isopropoxycarbonylmethylurea

HRID 1111011Notes

Reaction equation

HRID 1111011 reaction equation
ON=CC1C=CC([NH:10][C:11]([NH:13][CH2:14][C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])=[O:12])=CC=1.C[O-].[Na+].C(Br)C=C>O>[CH:18]([O:17][C:15]([CH2:14][NH:13][C:11](=[O:12])[NH2:10])=[O:16])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10942334Sodium MethoxideHCID 86744399N-[4-(hydroxyiminomethyl)phenyl]-N'-isopropoxycarbonylmethylurea

Product 1

HCID 21718770N'-isopropoxycarbonylmethylurea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of N-[4-(hydroxyiminomethyl)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 corresponding N-[4-allyloxyiminomethyl)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-eee3bdcdf69d42caa1c936c45da9e1f5
Source dataset
uspto-grants-1990_12
Patent number
US04977272

Reaction notes

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