Water → HCID 86612827, compound

HRID 1159645Notes

Reaction equation

HRID 1159645 reaction equation
[N:1]#[C:2][NH2:3].[C:4]([O-:7])([O-])=O.[K+].[K+].[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1.O>CN(C=O)C>[CH3:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:1]([CH2:16][C:15]2[CH:18]=[CH:19][C:12]([O:7][CH3:4])=[CH:13][CH:14]=2)[C:2]#[N:3])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9864CyanamideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 86612827HCID 86612827, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1 g of cyanamide in 50 ml of DMF is admixed with 13.1 g of K2CO3 and 6.5 ml of 4-methoxybenzyl chloride and then heated at 80° C. for 20 hours. After cooling to AT, the reaction mixture is poured into water, and extracted with AcOEt, the organic phase is dried over MgSO4 and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, eluting with an AcOEt/cyclohexane mixture (75/25; v/v). This gives 6.5 g of the expected compound in the form of an oil.

Workup

  1. temperatureAfter cooling to AT
  2. extractionextracted with AcOEt
  3. dry with materialthe organic phase is dried over MgSO4
  4. customthe solvent is evaporated under vacuum
  5. customThe residue is chromatographed on silica gel
  6. washeluting with an AcOEt/cyclohexane mixture (75/25; v/v)

Sources & evidence

ORD record
ord-fb35789e17ab4e1da38a70ede28f2334
Source dataset
uspto-grants-2010_10
Patent number
US07812165B2

Reaction notes

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