4-Chloro-3-nitrobenzoyl chloride → HCID 54918044, compound

HRID 605219Notes

Reaction equation

HRID 605219 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].Br.[NH2:15][C:16]1[S:17][C:18]([Br:21])=[CH:19][N:20]=1>N1C=CC=CC=1>[Br:21][C:18]1[S:17][C:16]([NH:15][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=2)=[N:20][CH:19]=1

Participants

4

Reactant 2

HCID 1234774-Chloro-3-nitrobenzoyl chlorideHCID 27238485-Bromothiazol-2-amine monohydrobromide

Product 1

HCID 54918044HCID 54918044, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-chloro-3-nitrobenzoyl chloride (1.539 g, 7.694 mmol) in anhydrous pyridine (40 mL) was treated with 2-amino-5-bromothiazole monohydrobromide (2.00 g, 7.694 mmol), and the reaction stirred under a nitrogen atmosphere at room temperature for 18 hours. The solvent was removed by rotary evaporation in vacuo and the oil dried on hi-vacuum. The residue was taken up in ethyl acetate (150 mL) and washed with water (4×50 mL) and brine (50 mL), then dried the organic phase over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Trituration with 6% ethyl acetate/methylene chloride afforded the title compound as a pinkish-tan solid (1.92 g, 69%).

Workup

  1. customThe solvent was removed by rotary evaporation in vacuo
  2. customthe oil dried on hi-vacuum
  3. washwashed with water (4×50 mL) and brine (50 mL)
  4. dry with materialdried the organic phase over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a8bad76ea9341c39f4040b8244f9e0a
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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