Diisopropylethylamine → HCID 22482293, compound

HRID 2181888Notes

Reaction equation

HRID 2181888 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[CH:16]([NH2:18])[CH3:17].[CH3:19][O:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=1[S:29](Cl)(=[O:31])=[O:30].C(N(CC)C(C)C)(C)C>ClCCl>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=1[S:29]([NH:18][CH:16]([C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])[CH3:17])(=[O:30])=[O:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27346262,4-Dimethoxybenzenesulfonyl chlorideHCID 22482308HCID 22482308, compound

Product 1

HCID 22482293HCID 22482293, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 1-(2′,4,4′-trifluoro-1,1′-biphenyl-2-yl)ethylamine (0.71 g, 2.84 mmol) in dichloromethane (5 mL) was treated with 2,4-dimethoxybenzenesulfonyl chloride (0.71 g, 3.0 mmol), and N,N-diisopropylethylamine (0.77 g, 6.0 mmol). The reaction was stirred at room temperature for twelve hours, and the solvent was evaporated in vacuo to a crude oil. The crude oil was purified by preparative liquid chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g), eluting with a gradient of between 5% and 50% methyl tert-butyl ether in hexane at a flow rate of 40 mL/min to afford, after evaporation of the solvent, a colorless oil. Crystallization of the colorless oil from ethyl acetate-hexane yielded the title compound (0.93 g, 2.07 mmol, 73%) as a homogeneous, colorless, crystalline solid, m.p. 192-194° C.;

Workup

  1. customthe solvent was evaporated in vacuo to a crude oil
  2. customThe crude oil was purified by preparative liquid chromatography on a Biotage® 40 Mi column of pre-packed silica gel (90 g)
  3. washeluting with a gradient of between 5% and 50% methyl tert-butyl ether in hexane at a flow rate of 40 mL/min
  4. customto afford
  5. customafter evaporation of the solvent
  6. customCrystallization of the colorless oil from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0a1c2a4739644f6980930d432ae6a2ee
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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