Methyl p-toluenesulfonate → N-methyl-4-benzyloxyphenylcyanamide

HRID 1464063Notes

Reaction equation

HRID 1464063 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]#[N:23])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.COS(C1C=CC(C)=CC=1)(=O)=O>CC(C)=O>[CH3:1][N:21]([C:18]1[CH:19]=[CH:20][C:15]([O:14][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:16][CH:17]=1)[C:22]#[N:23]

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 11430Potassium CarbonateHCID 190892954-Benzyloxyphenylcyanamide

Product 1

HCID 19089199N-methyl-4-benzyloxyphenylcyanamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Potassium carbonate (9.6 g) was added to a solution of 4-benzyloxyphenylcyanamide (6.3 g) in acetone (450 ml) with stirring. A solution of methyl-4-toluene sulphonate (9 g) in acetone (50 ml) was added and the mixture stirred for 7 hours. The solvent was removed by evaporation and the residue suspended in water and extracted into dichloromethane. The extract was dried (Na2SO4) and the solvent removed by evaporation to give a residue which was triturated with a 1:1 mixture of ethylacetate and hexane to give N-methyl-4-benzyloxyphenylcyanamide (m.p. 116° C.).

Workup

  1. stirringthe mixture stirred for 7 hours
  2. customThe solvent was removed by evaporation
  3. extractionextracted into dichloromethane
  4. dry with materialThe extract was dried (Na2SO4)
  5. customthe solvent removed by evaporation
  6. customto give a residue which
  7. customwas triturated with a 1:1 mixture of ethylacetate and hexane

Sources & evidence

ORD record
ord-dc9b6eb73df64018a8dd1952ee648c70
Source dataset
uspto-grants-1994_04
Patent number
US05302720

Reaction notes

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