4-Nitrobenzoyl chloride → HCID 22462664, compound

HRID 1387127Notes

Reaction equation

HRID 1387127 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[S:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[CH:4]=1.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14]>ClC1C=CC=CC=1>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([C:20]([C:4]2[C:5]3[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=3[S:7][C:3]=2[N:2]([CH3:12])[CH3:1])=[O:21])=[CH:23][CH:24]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 13926094HCID 13926094, compound

Product 1

HCID 22462664HCID 22462664, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 5.00 g (28.2 mmol) of 2-dimethylaminobenzo[b]thiophene (Vesterager et al., Tetrahedron, 1973, 29, 321-329) and 6.3 g (33.9 mmol) of 4-nitrobenzoyl chloride in 100 mL of chlorobenzene was heated at 105° C. for 6 h. The reaction was cooled and concentrated in vacuo. Purification of the residue by flash chromatography (SiO2; 5% then 10% then 25% EtOAc in hexanes) afforded 7.51 g (23.0 mmol; 82%) of the title compound as burgundy flakes.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. customPurification of the residue by flash chromatography (SiO2

Sources & evidence

ORD record
ord-9df5111aacfc4bc28ff26a0f7332433e
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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