4-Nitrobenzoyl chloride → 2-Dimethylamino-5-fluoro-6-methoxybenzo[b]thiophene-3-yl 4-Nitrophenyl Ketone

HRID 1387045Notes

Reaction equation

HRID 1387045 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]1[S:7][C:6]2[CH:8]=[C:9]([O:13][CH3:14])[C:10]([F:12])=[CH:11][C:5]=2[CH:4]=1.[N+:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([O-:18])=[O:17]>ClC1C=CC=CC=1.CCOC(C)=O>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([C:4]2[C:5]3[CH:11]=[C:10]([F:12])[C:9]([O:13][CH3:14])=[CH:8][C:6]=3[S:7][C:3]=2[N:2]([CH3:15])[CH3:1])=[O:24])=[CH:26][CH:27]=1)([O-:18])=[O:17]

Participants

5

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 107755692-Dimethylamino-5-fluoro-6-methoxybenzo[b]thiophene

Product 1

HCID 211828752-Dimethylamino-5-fluoro-6-methoxybenzo[b]thiophene-3-yl 4-Nitrophenyl KetoneYield 116.4%

Reagents, catalysts & solvents 2

HCID 7964ChlorobenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.08 g (4.82 mmol) of 2-dimethylamino-5-fluoro-6-methoxybenzo[b]thiophene (Part B) in 15 mL of chlorobenzene was treated with 0.99 g (5.31 mmol) of 4-nitrobenzoyl chloride. The reaction was stirred at room temperature for 17 h and was diluted with 100 mL of EtOAc. The solution was washed sequentially with 2 N aqueous NaOH (2×50 mL), H2O (50 mL) and brine (50 mL), then dried over Na2SO4, and filtered. Evaporation of the solvent in vacuo afforded 2.1 g of a dark solid which was purified by flash chromatography (SiO2; gradient of 10% then 20% then 40% EtOAc in hexanes) to give 0.27 g of starting material and 1.25 g (3.34 mmol; 93% based on consumed starting material) of the title compound.

Workup

  1. washThe solution was washed sequentially with 2 N aqueous NaOH (2×50 mL), H2O (50 mL) and brine (50 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-3bbbb3c2248640248fc79685b47ee6f3
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

Loading…