Cyanamidnatrium → HCID 178431161, compound

HRID 237867Notes

Reaction equation

HRID 237867 reaction equation
[N:1]#[C:2][NH2:3].[Na].[CH:5]1([C:11]2[CH:22]=[CH:21][C:14]([O:15][CH2:16][C:17]3([CH3:20])[CH2:19][O:18]3)=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>CO>[CH:5]1([C:11]2[CH:12]=[CH:13][C:14]([O:15][CH2:16][C:17]3([CH3:20])[O:18][C:2](=[NH:3])[NH:1][CH2:19]3)=[CH:21][CH:22]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 57375518CyanamidnatriumHCID 86640239HCID 86640239, compound

Product 1

HCID 178431161HCID 178431161, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (250 ml) and sodium hydrogen cyanamide (1.92 g, 30 mmol) were added to a flask containing 2-(4-cyclohexyl-phenoxymethyl)-2-methyl-oxirane (6.15 g, 25 mmol). The reaction mixture was stirred overnight at room temperature and then concentrated in vacuo. The residue was dissolved in methylene chloride and washed with water, then saturated potassium carbonate. The methylene chloride layer was dried over 4 A molecular sieves, filtered and concentrated in vacuo to yield 5.46 g of a white solid. The white solid was recrystallized from ether to yield 1.11 g of the title compound as white crystals. A second crop yielded 0.64 g of white crystals.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialThe methylene chloride layer was dried over 4 A molecular sieves
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29c29a6fc91e4085ac269d14df1803ac
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

Loading…