2,4,6-Trimethylbenzoyl chloride → 2,4,6-Trimethyl-N-(7-nitro-1,3-benzothiazol-2-yl)benzamide

HRID 2235499Notes

Reaction equation

HRID 2235499 reaction equation
[N+:1]([C:4]1[C:12]2[S:11][C:10]([NH2:13])=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:14][C:15]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[C:16]=1[C:17](Cl)=[O:18]>N1C=CC=CC=1>[CH3:14][C:15]1[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([CH3:25])[C:16]=1[C:17]([NH:13][C:10]1[S:11][C:12]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=[CH:7][C:8]=2[N:9]=1)=[O:18]

Participants

4

Reactant 2

HCID 970382,4,6-Trimethylbenzoyl chlorideHCID 43257247-Nitro-1,3-benzothiazol-2-amine

Product 1

HCID 860492022,4,6-Trimethyl-N-(7-nitro-1,3-benzothiazol-2-yl)benzamideYield 66%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
75 °C

Procedure

To 0.089 g (0.46 mmol) of 7-nitro-1,3-benzothiazol-2-amine in 1 mL of pyridine was added 0.17 g (0.91 mmol) of 2,4,6-trimethylbenzoyl chloride. The mixture was heated to 75° C. for 18 h and the volatiles were removed in vacuo. The residue was washed with water and 1 N hydrochloric acid, dissolved in ethyl acetate, dried over sodium sulfate, filtered, concentrated in vacuo and the resulting crude solid was purified by flash chromatography eluting with 25% ethyl acetate/hexanes mixture to give 0.103 g (66%) of the title compound as a tan solid.

Workup

  1. customthe volatiles were removed in vacuo
  2. washThe residue was washed with water and 1 N hydrochloric acid
  3. dissolutiondissolved in ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe resulting crude solid was purified by flash chromatography
  8. washeluting with 25% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-3a18adc1c6664865b192f20b25dfca42
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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