M-Phenylenediamine → (3-Amino-phenyl)-carbamic acid benzyl ester

HRID 2102959Notes

Reaction equation

HRID 2102959 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.C(N(CC)C(C)C)(C)C.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20].C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:7][C:3]1[CH:2]=[C:1]([NH:8][C:19](=[O:20])[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7935M-PhenylenediamineHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 516892Sodium Bicarbonate

Product 1

HCID 12941491(3-Amino-phenyl)-carbamic acid benzyl esterYield 71.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of m-phenylenediamine (5.0 g, 0.046 mol) and N,N-diisopropylethylamine (8.0 mL, 0.046 mol) in CH2Cl2 (150 mL) at 0° C. was added slowly benzyl chloroformate (6.6 mL, 0.046 mol). The mixture was stirred at 0° C. for 2 h and then warmed to rt for 2 h. Aq. NaHCO3 solution was added and the organic phase was separated, washed with brine, dried (Na2SO4) and concentrated. The residue was purified by column chromatography on silica gel to give the desired product (8.0 g, 71%) as a syrup. LC-MS: 2.11 min, 243.0 (M+1).

Workup

  1. temperaturewarmed to rt for 2 h
  2. customthe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2890c641f0b246c5bc08094e477e540e
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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