Allyl bromide → HCID 86743382, compound

HRID 1607835Notes

Reaction equation

HRID 1607835 reaction equation
[OH:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](=[O:15])[CH:13]([C:16]([O:18][CH3:19])=[O:17])[NH:12][C:11]2=[O:20])=[CH:6][CH:5]=1.[H-].[Na+].[H][H].[CH2:25](Br)[CH:26]=[CH2:27]>C(OCC)C.O>[CH2:27]([O:1][N:2]=[CH:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[CH:13]([C:16]([O:18][CH3:19])=[O:17])[NH:12][C:11]2=[O:20])=[CH:8][CH:9]=1)[CH:26]=[CH2:25]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 86743383HCID 86743383, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86743382HCID 86743382, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 0.01 mol of 3-[4-(hydroxyiminomethyl)phenyl]-5-methoxycarbonylhydantoin in diethyl ether is treated with 0.01 mol of sodium hydride. After hydrogen evolutionstops, 0.011 mol of allyl bromide is added. The reaction mixture is stirredfor 2 hours. The reaction mixture is then poured into cold water, the layers are separated, and the aqueous layer is extracted with diethyl ether. The combined ether solutions are dried over MgSO4 and filtered, and the solvent is removed by rotary evaporator to yield 3-[4-(allyloxyiminomethyl)phenyl]-5-methoxycarbonylhydantoin.

Workup

  1. customthe layers are separated
  2. extractionthe aqueous layer is extracted with diethyl ether
  3. dry with materialThe combined ether solutions are dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent is removed by rotary evaporator

Sources & evidence

ORD record
ord-75b53097b7324d6bb93b2c41539b3be7
Source dataset
uspto-grants-1989_09
Patent number
US04868061

Reaction notes

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