O-Cresol → HCID 21264593, compound

HRID 567122Notes

Reaction equation

HRID 567122 reaction equation
[H-].[Na+].[C:3]1([CH3:10])[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]([CH3:22])[C:20]#[N:21]>CN(C)C=O>[CH3:10][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N:19]([CH3:22])[C:20]#[N:21]

Participants

5

Reactant 3

HCID 335O-CresolHCID 24758Sodium hydrideHCID 21264584HCID 21264584, compound

Product 1

HCID 21264593HCID 21264593, compoundYield 124.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
20 °C

Procedure

1 g (0.024 mol) of a 60% sodium hydride suspension is suspended in 10 ml of dimethylformamide and admixed with a solution of 2.2 g (0.02 mol) of ortho-cresol in 10 ml of dimethylformamide, and the mixture is stirred at 20° C. for 40 minutes. A solution of 11.3 g (0.02 mol) of 40% pure N-(2-bromomethylphenyl)-N-methyl-cyanamide in 10 ml of dimethylformamide is added, and the mixture is stirred at 20° C. for 18 hours. The mixture is stirred into 200 ml of ice/sodium chloride solution and extracted with ether. The combined organic phases are dried over Na2SO4 and concentrated under reduced pressure. The residue is chromatographed over silica gel using cyclohexane/ethyl acetate (3:1). 6.3 g of N-[2-(2-methylphenoxymethyl)-phenyl]-N-methyl-cyanamide of a content of 40% (HPLC) are obtained.

Workup

  1. stirringthe mixture is stirred at 20° C. for 18 hours
  2. extractionextracted with ether
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-ab5da775cd2a494fb5ebd3ec95e9002f
Source dataset
uspto-grants-2001_01
Patent number
US06177459B1

Reaction notes

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