Aluminum(III) Chloride → HCID 45261438, compound

HRID 898414Notes

Reaction equation

HRID 898414 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]([NH:30][CH3:31])=[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]([N:30]([C:27]2[CH:28]=[CH:29][C:24]([CH:20]([CH2:22][CH3:23])[CH3:21])=[CH:25][CH:26]=2)[CH3:31])=[NH:17])=[CH:13][CH:14]=1)([CH2:7][CH3:8])[CH3:6].[ClH:1]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 22675640HCID 22675640, compoundHCID 22675643HCID 22675643, compound

Product 1

HCID 45261438HCID 45261438, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Aluminum chloride (0.39 g, 2.93 mmol) was added to a stirred solution of 4-sec-butylphenyl-N-methyl cyanamide (0.5 g, 2.66 mmol) in chlorobenzene (14 mL) at 145° C. After 10 minutes 4-sec-butylphenyl-N-methyl amine hydrochloride (0.466 g, 2.34 mmol; prepared from 4-sec-butylphenyl-N-methyl amine and 1.0 M HCl-ether) was added and continued reflux. After 5 hours, the reaction mixture was evaporated on rotavapor and the product was purified by flash chromatography using chloroform/methanol (10:1) to afford the title compound (0.34 g, 38%) as an extremely hygroscopic solid, mp: 65-66° C.; TLC: Rf=0.13 (CHCl3:CH3OH; 10:1); 1H NMR (CD3OD): δ 6.99 (d, 4H, J=8.46 Hz, ArH), 6.80 (d, 4H, J=8.34 Hz, ArH), 3.36 (s, 6H, 2×-NCH3), 2.50 (m, 2H, 2×—CH), 1.58-1.53 (m, 4H, 2×-CH2), 1.16 (d, 6H, 2×-CH3), 0.79 (t, 6H, J=7.35 Hz, 2×-CH3); HRMS: 351.2660 (351.2674 Calcd. for C23HH33N3); Anal.: C23H33N3·HCl; 1.75H2O (418.74); Calcd. (%): C, 66.19, H, 8.64; N, 10.07; Found (%): C, 66.56, H, 8.55; N, 11.27; HPLC: (CH3CN:H2O 50:50 with 0.1% TFA): 99% pure.

Workup

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

Sources & evidence

ORD record
ord-c09a12c626b8439cb5c644f5218f133e
Source dataset
uspto-grants-2008_04
Patent number
US07351743B1

Reaction notes

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