Sodium hydride → HCID 86743380, compound

HRID 1607831Notes

Reaction equation

HRID 1607831 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]([CH3:16])[NH:12][C:11]2=[O:17])=[CH:6][CH:5]=1.[H-].[Na+].[H][H].[CH2:22](Br)[CH:23]=[CH:24][CH3:25]>C(OCC)C.O>[CH2:22]([O:1][N:2]=[CH:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14](=[O:15])[CH:13]([CH3:16])[NH:12][C:11]2=[O:17])=[CH:8][CH:9]=1)[CH:23]=[CH:24][CH3:25]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 1224142-Butene, 1-bromo-HCID 86743381HCID 86743381, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86743380HCID 86743380, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 0.01 mol of 3-[4-(hydroxyiminomethyl)phenyl]-5-methylhydantoin in diethyl ether is treated with 0.01 mol of sodium hydride. After hydrogen evolution stops, 0.011 mol of crotyl bromide is added. The reaction mixture is stirred for 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-(crotyloxyiminomethyl)phenyl]-5-methylhydantoin.

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-7fd74c089a2a466290e85c0e5183411a
Source dataset
uspto-grants-1989_09
Patent number
US04868061

Reaction notes

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