Isopropylamine → HCID 86612014, compound

HRID 2234157Notes

Reaction equation

HRID 2234157 reaction equation
Cl[C:2]1[C:7]([C:8]2[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:15])=[C:6]([Cl:16])[N:5]=[C:4]([S:17][CH3:18])[N:3]=1.[CH:19]([NH2:22])([CH3:21])[CH3:20]>ClCCl>[Cl:16][C:6]1[N:5]=[C:4]([S:17][CH3:18])[N:3]=[C:2]([NH:22][CH:19]([CH3:21])[CH3:20])[C:7]=1[C:8]1[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:15]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 22325510HCID 22325510, compound

Product 1

HCID 86612014HCID 86612014, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

A solution of 37.5 g (324 mmol) of the product of step b in 150 ml of anhydrous dichloromethane was treated with 24 g (406 mol) of isopropylamine and stirred for five hours at approximately 20 to 25° C. Then, the solvent was distilled off, the residue was taken up in ethyl acetate and washed with dilute HCl, water and dilute NaHCO3 solution, dried and freed from solvent. Following chromatography on silica gel (cyclohexane/methyl tert-butyl ether 100:1 to 19:1), 13.4 g of the title compound were obtained from the residue in the form of colorless crystals of m.p. 94-98° C., which were employed in the next step without further purification.

Workup

  1. distillationThen, the solvent was distilled off
  2. washwashed with dilute HCl, water and dilute NaHCO3 solution
  3. customdried

Sources & evidence

ORD record
ord-80560718770c4825a377288fa07b0390
Source dataset
uspto-grants-2010_05
Patent number
US07709637B2

Reaction notes

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