3-Nitroaniline → HCID 372837, compound

HRID 2057064Notes

Reaction equation

HRID 2057064 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[N+:10]([C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16])([O-:12])=[O:11].[OH-].[Na+]>CC(C)=O>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([NH:16][C:15]2[CH:17]=[CH:18][CH:19]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=2)[N:7]=1

Participants

5

Reactant 3

HCID 74233-NitroanilineHCID 7954Cyanuric chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 372837HCID 372837, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To cyanuric chloride (1.3307 g, 7.2 mmol) dissolved in acetone (15 mL) stirring at 0-5° C., was added a solution of 3-nitroaniline (1.0023 g, 7.2 mmol) in acetone (15 mL) followed by the addition of 2.5 N NaOH (2.9 mL, 7.2 mmol). The reaction mixture was allowed to stir at 0-5° C. for 1 hour under nitrogen. The reaction mixture was poured over crushed ice. The solid that formed was collected by vacuum filtration and the resulting solid was dried overnight under vacuum. The product was used with no further purification, (158a, 2.01 g, 98%), mp 173° C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 21.5 min, 97.1% purity; MS (TOF MS ES+): m/z 370 (80.33), 291 (43.4), 286 (M+H, 100).

Workup

  1. stirringto stir at 0-5° C. for 1 hour under nitrogen
  2. additionThe reaction mixture was poured
  3. customover crushed ice
  4. customThe solid that formed
  5. filtrationwas collected by vacuum filtration
  6. customthe resulting solid was dried overnight under vacuum
  7. customThe product was used with no further purification, (158a, 2.01 g, 98%), mp 173° C.

Sources & evidence

ORD record
ord-7cba878817db40debea9f63d5f205522
Source dataset
uspto-grants-2008_02
Patent number
US07335770B2

Reaction notes

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