Water → HCID 64592025, compound

HRID 1817914Notes

Reaction equation

HRID 1817914 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[C:12](Cl)(=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14].C(N(CC)C(C)C)(C)C.O>ClCCl.CN(C)C1C=CN=CC=1>[Cl:11][C:8]1[CH:9]=[CH:10][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([NH:6][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 62493Pivaloyl chlorideHCID 742185-Chloro-2-nitroanilineHCID 81531Diisopropylethylamine

Product 1

HCID 64592025HCID 64592025, compoundYield 34.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-nitro-5-chloroaniline (Tokyo Kasei Kogyo Co., Ltd., 3 g, 17.4 mmol), pivaloyl chloride (2.1 mL, 17.4 mmol) and N,N-diisopropylethylamine (3.1 mL, 17.4 mmol) in dichloromethane (80 mL) was stirred at room temperature for 20 h. 4-Dimethylaminopyridine (531 mg, 4.4 mmol) was added and the stirring was continued for 3 days. The mixture was poured into water (30 mL) and the mixture was extracted with dichloromethane (30 mL). After removal of solvent, the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:20 as eluent) to afford the title compound (1.54 g, 34%) as a pale yellow solid.

Workup

  1. waitthe stirring was continued for 3 days
  2. extractionthe mixture was extracted with dichloromethane (30 mL)
  3. customAfter removal of solvent
  4. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:20 as eluent)

Sources & evidence

ORD record
ord-3bf4dd5e1567411abfb3f112dec55148
Source dataset
uspto-grants-2009_10
Patent number
US07598393B2

Reaction notes

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