Pyridine → HCID 44203196, compound

HRID 1919608Notes

Reaction equation

HRID 1919608 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].N1C=CC=CC=1.[Cl:18][C:19]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:20]=1[C:21](Cl)=[O:22]>ClCCl>[Cl:18][C:19]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:20]=1[C:21]([NH:7][C:6]1[CH:8]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10])=[O:22]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 742185-Chloro-2-nitroanilineHCID 117637Benzoyl chloride, 2-chloro-5-nitro-

Product 1

HCID 44203196HCID 44203196, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

5-Chloro-2-nitroaniline (1 g; 5.8 mmol) and pyridine (0.64 ml; 8.1 mmol) were dissolved in dichloromethane (10 ml) and cooled to 0° C. This was added drop wise over 5 minutes to a solution of 2-chloro-5-nitrobenzoyl chloride (1.34 g; 6.1 mmol) in dichloromethane (5 ml). The reaction was stirred at room temperature for 72 hours before adding further acid chloride (1.34 g) and pyridine (0.64 ml). After 30 minutes, the solvent was evaporated and the bisacylated residue treated with 1:1 concentrated ammonia/acetonitrile (10 ml). All the solvent was removed after 5 minutes and the residue crystallised from 1:1 chloroform/heptane (30 ml) to give 2-chloro-N-(5-chloro-2-nitro-phenyl)-5-nitro-benzamide (1.78 g, 86%)

Workup

  1. waitAfter 30 minutes
  2. customthe solvent was evaporated
  3. additionthe bisacylated residue treated with 1:1 concentrated ammonia/acetonitrile (10 ml)
  4. customAll the solvent was removed after 5 minutes
  5. customthe residue crystallised from 1:1 chloroform/heptane (30 ml)

Sources & evidence

ORD record
ord-1ad70fd3172c4adda99989f1148d2f52
Source dataset
uspto-grants-2012_05
Patent number
US08168653B2

Reaction notes

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