4-Nitroaniline → HCID 178526680, compound

HRID 266906Notes

Reaction equation

HRID 266906 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:11][N:12]1[N:17]=[C:16](Cl)[CH:15]=[C:14]([Cl:19])[NH:13]1.ClC1N=NN=C(Cl)C=1Cl.C(=O)(O)[O-].[Na+]>O.CC(C)=O>[Cl:11][N:12]1[N:13]=[C:14]([Cl:19])[CH:15]=[C:16]([NH:8][C:7]2[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[NH:17]1

Participants

7

Reactant 4

HCID 74754-Nitroaniline3×HCID 516892Sodium BicarbonateHCID 124936114,5,6-Trichloro-1,2,3-triazineHCID 21988082HCID 21988082, compound

Product 1

HCID 178526680HCID 178526680, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

Para-nitroaniline (13.8 g) was dissolved into acetone (150 ml) at room temperature. 2,4,6-Trichlorotriazine (18.4 g) was dissolved into acetone (100 ml). Then the trichlorotriazine solution was dropwisely added to the p-nitroaniline solution as the p-nitroaniline solution was cooled with iced water. After the reaction was carried out for 2 hours at 0° C., an aqueous sodium bicarbonate solution (8.4 g of sodium bicarbonate being dissolved in 100 ml of water) was dropwisely added to the solution over 30 minutes. Then, the cooling was stopped by removing the ice bath and the solution was stirred until the temperature of the solution became room temperature. The reaction product was filtered off, washed with water and vacuum dried to obtain 23 g of 2,4-dichloro-6-p-nitroanilinotriazine. The chemical structure of the reaction product was confirmed by NMR and the melting point.

Workup

  1. customby removing the ice bath
  2. custombecame room temperature
  3. filtrationThe reaction product was filtered off
  4. washwashed with water and vacuum
  5. customdried

Sources & evidence

ORD record
ord-c5ffaf95e79648d2b17e8197db5f8b98
Source dataset
uspto-grants-1997_07
Patent number
US05652327

Reaction notes

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