ethyl N-ethoxycarbonyliminocarbamate → [2-(2-Benzoyl-phenyldisulfanyl)-phenyl]-phenylmethanone

HRID 3746

Reaction equation

HRID 3746 reaction equation
[SH:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].N(C([O:25][CH2:26][CH3:27])=O)=NC(OCC)=O>C(OCC)C.C1C=CC=CC=1>[C:4]([C:3]1[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=1[S:1][S:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:26]([C:27]1[CH:10]=[CH:11][CH:6]=[CH:7][CH:8]=1)=[O:25])(=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 34997132-Mercaptobenzophenone

Product 1

HCID 18935315[2-(2-Benzoyl-phenyldisulfanyl)-phenyl]-phenylmethanoneYield 50.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-mercaptobenzophenone (2.3 g, 7.4 mmol) in diethyl ether (10 mL) was added dropwise diethyl azodicarboxylate (0.65 g, 3.7 mmol). The solution was stirred for 5 minutes at room temperature, then diluted with benzene (40 mL) and refluxed for 16 hours. The solution was cooled and concentrated in vacuo leaving a yellow liquid. The crude product was purified using silica gel chromatography (75% hexane/25% ethyl acetate) to give the title compound as a yellow foam (0.8 g, 50%);

Workup

  1. temperaturerefluxed for 16 hours
  2. temperatureThe solution was cooled
  3. concentrationconcentrated in vacuo
  4. customleaving a yellow liquid
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-950cfed0e8884a9ab3f2f0fdcbee3869
Source dataset
uspto-grants-1998_03
Patent number
US05734081

Linked notes

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