Citric Acid → methyl N-(3-phenylbenzyl)carbamate

HRID 1168027Notes

Reaction equation

HRID 1168027 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH2:10][NH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.Cl[C:22]([O:24][CH3:25])=[O:23].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=2)[CH2:10][NH:11][C:22](=[O:23])[O:24][CH3:25])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 1049PyridineHCID 6586Methyl chloroformateHCID 27603683-(Aminomethyl)biphenyl

Product 1

HCID 12090300methyl N-(3-phenylbenzyl)carbamateYield 58.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

11.18 g of 3-phenylbenzylamine in toluene (250 ml) was mixed with 7.24 g of pyridine at room temperature. The resulting solution was stirred under cooling with ice while 9.58 g of methyl chloroformate was added dropwise and then stirred at room temperature for 2 hours. After the reaction, the reaction solution was poured into aqueous citric acid and extracted with ethyl acetate, and the organic layer was washed with aqueous citric acid, 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 8.61 g of methyl N-(3-phenylbenzyl)carbamate as pale yellow crystals. m.p. 49-52° C.

Workup

  1. additionwas added dropwise
  2. stirringstirred at room temperature for 2 hours
  3. customAfter the reaction
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was washed with aqueous citric acid
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated under reduced pressure for removal of the solvent
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a1285b3940f24773b44f1671059f4816
Source dataset
uspto-grants-2003_09
Patent number
US06620961B1

Reaction notes

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