Triphosgene → HCID 22467342, compound

HRID 1934648Notes

Reaction equation

HRID 1934648 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:6][NH:7][C:8](=[O:24])[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[NH:18][CH:19]([CH2:22][OH:23])[CH2:20][OH:21].Cl[C:31](Cl)([O:33]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:6][NH:7][C:8](=[O:24])[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[NH:18][CH:19]1[CH2:22][O:23][C:31](=[O:33])[O:21][CH2:20]1

Participants

6

Reactant 2

HCID 94429TriphosgeneHCID 22467487HCID 22467487, compound

Product 1

HCID 22467342HCID 22467342, compoundYield 180.7%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3,4-dimethoxybenzyl)-2-[2-hydroxy-1-(hydroxymethyl)ethylamino]-5-nitrobenzamide (134 mg) in a mixture of dichloromethane (1 mL) and pyridine (1 mL) was added triphosgene (49.1 mg) at −78° C. Then, the resulting mixture was stirred for an hour at ambient temperature. The mixture was diluted with ethyl acetate and washed successively with diluted ammonium chloride, water and brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was subjected to a silica gel column chromatography eluting with a mixture of chloroform and ethyl acetate (7:3) to give N-(3,4-dimethoxybenzyl)-5-nitro-2-(2-oxo-1,3-dioxan-5-ylamino)benzamide (129 mg) as a solid substance.

Workup

  1. washwashed successively with diluted ammonium chloride, water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated in vacuo
  4. washeluting with a mixture of chloroform and ethyl acetate (7:3)

Sources & evidence

ORD record
ord-d36993430127417bacd66cb020189e07
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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