4-Toluenesulfonyl chloride → 2-[3-Bromophenyl]-N-(4-methylphenylsulphonyl)ethylamine

HRID 11428Notes

Reaction equation

HRID 11428 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C1COCC1>[Br:2][C:3]1[CH:4]=[C:5]([CH:9]([S:26]([C:23]2[CH:24]=[CH:25][C:20]([CH3:19])=[CH:21][CH:22]=2)(=[O:28])=[O:27])[CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 693553312-(3-Bromophenyl)ethanamine hydrochloride

Product 1

HCID 693535362-[3-Bromophenyl]-N-(4-methylphenylsulphonyl)ethylamineYield 68.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Bromophenylethylamine hydrochloride (9.44 g) was added to THF (60 ml) containing triethylamine (12.24 ml) and stirred-under argon at 5° C. during the portionwise addition over 15 minutes of 4-methylphenylsulphonyl chloride (11.44 g). The slurry was diluted with THF (50 ml) and stirred for 16 h. The solid was filtered off, washed with THF and the filtrate evaporated. The residue was dissolved in ethyl acetate, washed with 1N hydrochloric acid, water, brine and dried (MgSO4). Chromatography on flash silica, eluting with 0 to 25% ethyl acetate in isohexane gave the product (9.67 g).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with THF
  3. customthe filtrate evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 1N hydrochloric acid, water, brine
  6. dry with materialdried (MgSO4)
  7. washChromatography on flash silica, eluting with 0 to 25% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-760b60ae9f0d4a8cb3a157644a6f1fab
Source dataset
uspto-grants-2006_08
Patent number
US07098240B2

Reaction notes

Loading…