Phosgene → HCID 22174927, compound

HRID 1864515Notes

Reaction equation

HRID 1864515 reaction equation
[NH2:1][C:2]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])=[O:5].[C:24](Cl)(Cl)=[O:25]>C1(C)C=CC=CC=1>[Cl:16][C:10]1[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][N:6]1[C:4](=[O:5])[C:3]2[C:2](=[CH:20][C:19]([N+:21]([O-:23])=[O:22])=[CH:18][CH:17]=2)[NH:1][C:24]1=[O:25]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 22175022HCID 22175022, compound

Product 1

HCID 22174927HCID 22174927, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2-amino-N-[2-(2,4-dichlorophenyl)ethyl]-4-nitrobenzamide (1.0 g, 2.82 mmol) in toluene (30 mL) was added a 1.9 M solution of phosgene in toluene (4.5 mL, 8.5 mmol). The reaction mixture was heated to 60° C. and stirred for 4 hours. The solvent was removed under reduced pressure and CH2Cl2 was added to the residue. The precipitate was collected via vacuum filtration and washed with CH2Cl2 to give the product (0.92 g, 86% yield) as a white solid. HPLC retention time: 3.28 min; Method A; LRMS (ESI) m/z 378 (M−1).

Workup

  1. customThe solvent was removed under reduced pressure and CH2Cl2
  2. additionwas added to the residue
  3. filtrationThe precipitate was collected via vacuum filtration
  4. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-8c4cb2baf90b4838ba825fd63ee2ff89
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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