Benzyl chloroformate → HCID 18964311, compound

HRID 2254541Notes

Reaction equation

HRID 2254541 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].Cl.[CH2:13]([N:15]([CH2:23][CH3:24])[C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1)[CH3:14].C(=O)([O-])O.[Na+]>ClCCl>[CH2:5]([O:4][C:2]([NH:22][C:19]1[CH:18]=[CH:17][C:16]([N:15]([CH2:23][CH3:24])[CH2:13][CH3:14])=[CH:21][CH:20]=1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 751451,4-Benzenediamine, N1,N1-diethyl-, hydrochloride (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 18964311HCID 18964311, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl chloroformate (15.7 mL, 0.11 mol) was added dropwise to a stirred mixture of N,N-diethyl-p-phenylenediamine hydrochloride (20 g, 0.1 mol) and sodium hydrogen carbonate (42.0 g) in dichloromethane at room temperature under nitrogen. After 16 hours at room temperature, the precipitate which had formed was removed by filtration. The solid residue was washed with dichloromethane and the combined dichloromethane extracts were concentrated to produce a brown oil. This material was purified by preparative high pressure liquid chromatography (hereinafter HPLC) on silica gel eluting with 10% hexanes/dichloromethane followed by dichloromethane alone. The resultant oil was triturated with hexanes to give N-benzyloxycarbonyl-4-diethylaminoaniline (18.25 g, 61% yield) as a crystalline solid. The structure of this compound was confirmed by mass spectroscopy and by 1H NMR spectroscopy.

Workup

  1. customthe precipitate which had formed
  2. customwas removed by filtration
  3. washThe solid residue was washed with dichloromethane
  4. concentrationthe combined dichloromethane extracts were concentrated
  5. customto produce a brown oil
  6. customThis material was purified by preparative high pressure liquid chromatography (hereinafter HPLC) on silica gel eluting with 10% hexanes/dichloromethane
  7. customThe resultant oil was triturated with hexanes

Sources & evidence

ORD record
ord-99a1a1341e5c410b9ebcaafb3fa4c358
Source dataset
uspto-grants-1993_08
Patent number
US05236884

Reaction notes

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