Dinitrofluorobenzene → N-(3-(2-Thiazolyl)phenyl)-2,4-dinitroaniline

HRID 581955Notes

Reaction equation

HRID 581955 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1F)([O-:3])=[O:2].[S:14]1[CH:18]=[CH:17][N:16]=[C:15]1[C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22].C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[S:14]1[CH:18]=[CH:17][N:16]=[C:15]1[C:19]1[CH:20]=[C:21]([NH:22][C:5]2[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 6264DinitrofluorobenzeneHCID 11430Potassium CarbonateHCID 110193903-(1,3-Thiazol-2-yl)aniline

Product 1

HCID 54468810N-(3-(2-Thiazolyl)phenyl)-2,4-dinitroaniline

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,4-dinitrofluorobenzene (1.14 ml, 9.1 mmol), 2t from Example 2 (1.6 g, 9.1 mmol) and potassium carbonate (1.51 g, 10.9 mmol) in dry N-methyl-2-pyrrolidone (10 ml) is heated to 80° C. for 2 hours. The cooled mixture is poured into ice-water. The precipitate is filtered off, washed with water and dried to yield: 3.05 g (98%). Mp 1 97-203° C.

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed with water
  3. customdried to yield: 3.05 g (98%)
  4. customMp 1 97-203° C.

Sources & evidence

ORD record
ord-fefc9efd0c094949b05eb83ee7e028b7
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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