Water → HCID 66687186, compound

HRID 69365

Reaction equation

HRID 69365 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:9](=[O:16])[NH:8][C:7]2=[O:17].I[CH:19]([CH3:21])[CH3:20].O>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:9](=[O:16])[N:8]([CH:19]([CH3:21])[CH3:20])[C:7]2=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 28011294-Chloro-5-nitrophthalimide

Product 1

HCID 66687186HCID 66687186, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (5.30 g, 0.132 mol) was added in portions to a solution of 5-chloro-6-nitroisoindoline-1,3-dione (20.0 g, 88.27 mmol) in 100 mL of anhydrous DMF at 0° C. under argon. The reaction mixture was then stirred at rt for 3 h. 2-Iodopropane (15.0 g, 106 mol) was added dropwise via a syringe at rt under argon. The resulted mixture was stirred for 6 h at rt, hydrolyzed by adding 200 mL of water. The precipitate was isolated, washed with water and dried under vacuum. The solid was purified by column chromatography (silica-gel, CH2Cl2/Acetone=19/1 v/v) to give a solid product.

Workup

  1. stirringThe resulted mixture was stirred for 6 h at rt
  2. customThe precipitate was isolated
  3. washwashed with water
  4. customdried under vacuum
  5. customThe solid was purified by column chromatography (silica-gel, CH2Cl2/Acetone=19/1 v/v)
  6. customto give a solid product

Sources & evidence

ORD record
ord-4d2c04b712974ce4ae0be93fe4c1faa6
Source dataset
uspto-grants-2014_09
Patent number
US08822500B2

Linked notes

Loading…