Methanol → methyl N-(2-methyl-3-phenylbenzyl)carbamate

HRID 1168032Notes

Reaction equation

HRID 1168032 reaction equation
[CH3:1][C:2]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[O-:16][C:17]#N.[K+].CO.O.C[N:24](C)[CH:25]=[O:26]>>[CH3:1][C:2]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH:24][C:25](=[O:26])[O:16][CH3:17]

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 6228DimethylformamideHCID 11378442Potassium cyanateHCID 147188083-(Bromomethyl)-2-methyl-1,1'-biphenyl

Product 1

HCID 12090307methyl N-(2-methyl-3-phenylbenzyl)carbamate

Procedure

3.57 g of 2-methyl-3-phenylbenzyl bromide, 1.66 g of potassium cyanate and 7.00 g of methanol in N,N-dimethylformamide (30 ml) were stirred at 80° C. for 5 hours. After the reaction, the reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was separated, dried over anhydrous magnesium sulfate and evaporated under reduced pressure for removal of the solvent. The residue was purified by silica gel column chromatography to give 2.01 g of methyl N-(2-methyl-3-phenylbenzyl)carbamate as colorless crystals. m.p. 91-94° C.

Workup

  1. customAfter the reaction
  2. extractionextracted with ethyl acetate
  3. customthe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure for removal of the solvent
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2fd240bb909244358f0e14dc9e319237
Source dataset
uspto-grants-2003_09
Patent number
US06620961B1

Reaction notes

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