Pyridine → HCID 18365510, compound

HRID 380642Notes

Reaction equation

HRID 380642 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)=[CH:3][CH:2]=1.N1C=CC=CC=1.[Cl:21][C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Cl:14][C:10]1[CH:9]=[C:8]([N:7]([C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)[C:22]([Cl:21])=[O:24])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 75453-ChlorodiphenylamineHCID 94429Triphosgene

Product 1

HCID 18365510HCID 18365510, compoundYield 258.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chlorodiphenylamine (3.0 g) and pyridine (1.43 mL) in CH2Cl2 (30 mL) was added triphosgene (1.75 g) at 5° C. After stirring at room temperature for 6 hours, the mixture was evaporated, diluted with EtOAc, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 15:1) to give N-(3-chlorophenyl)-N-phenylcarbamoyl chloride (4.05 g) as an oil.

Workup

  1. customthe mixture was evaporated
  2. additiondiluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 15:1)

Sources & evidence

ORD record
ord-a9e957e95e7f41caac5463b50284bc99
Source dataset
uspto-grants-2001_10
Patent number
US06303649B1

Reaction notes

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