4-Chloro-3-nitrobenzoyl chloride → N-(5-tert-Butyl-thiazol-2-yl)-4-chloro-3-nitro-benzamide

HRID 605187Notes

Reaction equation

HRID 605187 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].[NH2:14][C:15]1[S:16][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:18][N:19]=1>N1C=CC=CC=1>[C:20]([C:17]1[S:16][C:15]([NH:14][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:19][CH:18]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 1234774-Chloro-3-nitrobenzoyl chlorideHCID 6764855-tert-Butyl-1,3-thiazol-2-amine

Product 1

HCID 86615551N-(5-tert-Butyl-thiazol-2-yl)-4-chloro-3-nitro-benzamideYield 78%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-chloro-3-nitrobenzoyl chloride (1.336 g, 6.681 mmol) in anhydrous pyridine (30 mL) was treated with 2-amino-5-tert-butylthiazole (1.044 g, 6.681 mmol) and the reaction stirred at room temperature under a nitrogen atmosphere. The solvent was removed by rotary evaporation in vacuo and the residue dried on a vacuum pump. The residue was taken up in ethyl acetate (100 mL) and washed with water (4×50 mL) and brine (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification by silica gel chromatography eluting with 5% ethyl acetate/methylene chloride provided the title compound (1.76 g, 78%).

Workup

  1. customThe solvent was removed by rotary evaporation in vacuo
  2. customthe residue dried on a vacuum pump
  3. washwashed with water (4×50 mL) and brine (50 mL)
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel chromatography
  8. washeluting with 5% ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-bdb3f2ad895c41f893fb092db94c3afb
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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