Aluminum(III) Chloride → HCID 178441021, compound

HRID 898413Notes

Reaction equation

HRID 898413 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].[CH:5]([C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH3:18])[C:16]#[N:17])=[CH:11][CH:10]=1)([CH2:7][CH3:8])[CH3:6].Cl.[CH:20]([C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1)([CH2:22][CH3:23])[CH3:21]>ClC1C=CC=CC=1>[CH:5]([C:9]1[CH:10]=[CH:11][C:12]([N:15]([CH3:18])[C:16]([NH:30][C:27]2[CH:28]=[CH:29][C:24]([CH:20]([CH2:22][CH3:23])[CH3:21])=[CH:25][CH:26]=2)=[NH:17])=[CH:13][CH:14]=1)([CH2:7][CH3:8])[CH3:6].[ClH:1]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 22675643HCID 22675643, compoundHCID 22675818HCID 22675818, compound

Product 1

HCID 178441021HCID 178441021, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Aluminum chloride (0.42 g, 3.1 mmol) was added to a stirred solution of N-4-sec-butylphenyl-N-methyl cyanamide (0.534 g, 2.84 mmol) in chlorobenzene (15 mL) at 145° C. After 10 minutes 4-sec-butylphenyl amine hydrochloride (0.474 g, 2.56 mmol, prepared from 4-sec-butyl aniline and 1.0 M HCl-ether) was added and continued reflux. After 2 hours, the reaction mixture was evaporated and the product was purified by flash chromatography to afford the title compound (0.45 g, 65%) as a syrup. TLC: Rf=0.22 (CH2Cl2:CH3OH; 10:1); 1H NMR (CD3OD): δ 7.27 (d, 4H, J=8.18 Hz, ArH), 7.20 (d, 4H, J=8.36 Hz, ArH), 3.46 (s, 3H, —NCH3), 2.69-2.58 (m, 2H, 2×-CH), 1.68-1.57 (m, 4H, 2×-CH2), 1.25 (d, 6H, 2×-CH3), 0.85 (t, 6H, 2×-CH3); HRMS: 337.2484 (337.2528 Calcd. for C22H31N3); HPLC: (CH3CN:H2O; 50:50 with 0.1% TFA): 98% pure.

Workup

  1. temperaturecontinued reflux
  2. customthe reaction mixture was evaporated
  3. customthe product was purified by flash chromatography

Sources & evidence

ORD record
ord-befd677df6b745779493c94d87a276ca
Source dataset
uspto-grants-2008_04
Patent number
US07351743B1

Reaction notes

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