Benzyl chloroformate → HCID 18964311, compound

HRID 2227009Notes

Reaction equation

HRID 2227009 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-aa076bc14e264ca1aee19e6667667388
Source dataset
uspto-grants-1994_09
Patent number
US05350870

Reaction notes

Loading…