Thionyl Chloride → 2-Chloro-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dione

HRID 527127Notes

Reaction equation

HRID 527127 reaction equation
O[C:2]1([C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][C:17]=2[O:25][CH3:26])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-:14])=[O:13])[C:3]1=[O:15].S(Cl)([Cl:29])=O>>[Cl:29][C:2]1([C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][C:17]=2[O:25][CH3:26])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-:14])=[O:13])[C:3]1=[O:15]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 714769702-Hydroxy-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dione

Product 1

HCID 714769712-Chloro-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dioneYield 77%

Procedure

2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dione (1.00 g, 2.8 mmol) was dissolved in excess of thionyl chloride (10 ml), stirred at room temperature for 2 hrs. The reaction mixture was concentrated in a vacuum, and extracted with aq. sodium bicarbonate and ethylacetate. The organic layer was concentrated to afford the title compound (1.05 g, 77%).

Workup

  1. concentrationThe reaction mixture was concentrated in a vacuum
  2. extractionextracted with aq. sodium bicarbonate and ethylacetate
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-a1f89d4bceda4e7da518eedbf5bbc178
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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