Methyl iodide → HCID 21251015, compound

HRID 1531844Notes

Reaction equation

HRID 1531844 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:13][CH2:12][NH:11][C:10]1=[S:14].[H-].[Na+].[CH3:17]I>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:13]=[CH:12][N:11]=[C:10]1[S:14][CH3:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 570963221-(2-Methoxyphenyl)-2-imidazolidinethione

Product 1

HCID 21251015HCID 21251015, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 8.1 g (0.039 mol) of this 1-(2-methoxyphenyl)imidazoline-2-thione in 88 ml of dimethylformamide is added dropwise, under nitrogen at 0° C., to a suspension of 1.19 g (0.047 mol) of sodium hydride (95%) in 88 ml of anhydrous dimethylformamide. The reaction mixture is stirred for ¾ h at 0° C. 2.7 ml (0.043 mol) of methyl iodide previously diluted in 24 ml of dimethylformamide are added and the mixture is stirred for 1 hour at 0° C. The reaction mixture is poured over ice, extracted three times with ethyl acetate and washed twice with water and then with brine. The product is dried over magnesium sulphate, filtered and concentrated. 8.6 g of oil are obtained.

Workup

  1. additionare added
  2. stirringthe mixture is stirred for 1 hour at 0° C
  3. additionThe reaction mixture is poured over ice
  4. extractionextracted three times with ethyl acetate
  5. washwashed twice with water
  6. dry with materialThe product is dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-575d18994a004fda81191a99c31e7bf4
Source dataset
uspto-grants-2001_03
Patent number
US06200991B1

Reaction notes

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