4-Fluoro-3-nitrobenzoic acid → 3-Nitro-4-(3-thiazol-2-yl-phenylamino)benzoic acid

HRID 2262732Notes

Reaction equation

HRID 2262732 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([NH2:12])[CH:9]=[CH:10][CH:11]=1.F[C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24]>CN1C(=O)CCC1.O>[N+:23]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:14]=1[NH:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:2]2[S:1][CH:5]=[CH:4][N:3]=2)[CH:7]=1)[C:18]([OH:20])=[O:19])([O-:25])=[O:24]

Participants

5

Reactant 2

HCID 679874-Fluoro-3-nitrobenzoic acidHCID 110193903-(1,3-Thiazol-2-yl)aniline

Product 1

HCID 575722503-Nitro-4-(3-thiazol-2-yl-phenylamino)benzoic acidYield 83.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 3-thiazol-2-yl-phenylamine (14.0 g, 79 mmol) in anhydrous NMP (50 ml) was added 4-fluoro-3-nitrobenzoic acid (15.0 g, 127 mmol). The resultant mixture was stirred at 90° C. over night. The cooled reaction cake was suspended in water and the solid was filtered off, washed with water and dried in the air to afford the desired product (22.5 g, 83%).

Workup

  1. customThe cooled reaction cake
  2. filtrationthe solid was filtered off
  3. washwashed with water
  4. customdried in the air

Sources & evidence

ORD record
ord-6e4db7c9b4af47d48f91526c47b2ec4b
Source dataset
uspto-grants-2010_12
Patent number
US07851490B2

Reaction notes

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