4-Toluenesulfonyl chloride → HCID 18918564, compound

HRID 1290475Notes

Reaction equation

HRID 1290475 reaction equation
Cl.[C:2]([C:5]1[CH:13]=[CH:12][C:8]([CH2:9][CH2:10][NH2:11])=[CH:7][CH:6]=1)(=[O:4])[CH3:3].C(N(CC)CC)C.[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>ClCCl>[C:2]([C:5]1[CH:13]=[CH:12][C:8]([CH2:9][CH2:10][NH:11][S:28]([C:25]2[CH:26]=[CH:27][C:22]([CH3:21])=[CH:23][CH:24]=2)(=[O:30])=[O:29])=[CH:7][CH:6]=1)(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 138260051-[4-(2-aminoethyl)phenyl]Ethanone hydrochloride

Product 1

HCID 18918564HCID 18918564, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
4 °C

Procedure

To a stirred suspension under argon of 4-acetylphenethylamine hydrochloride (1 g) in dichloromethane (20 ml) was added triethylamine (0.94 ml) and stirring continued for 15 minutes. The mixture was cooled to 4° C., then 4-methylphenylsulphonyl chloride (1.29 g) in dichloromethane (5 ml) added dropwise over 30 minutes. The reaction mixture was stirred for 18 hours at ambient temperatuLe, then diluted with further dichloromethanie (50 ml), washed with water, dried (MgSO4) and evaporated. Trituration of the residue gave N-(2-[4-acetylphenyl]ethyl)-4-methylphenylsulphonamide, 1.58 g, as a yellow crystalline solid: m.p. 124°-126° C.; NMR (d6 DMSO) δ 7.84(2H,d), 7.63(3H,m), 7.37(2H,d), 7.29(2H,d), 2.98(2H,q), 2.75(2H,t), 2.55(3H,s), 2.39(3H,s); m/e 318(M+H)+.

Workup

  1. stirringThe reaction mixture was stirred for 18 hours at ambient temperatuLe
  2. additiondiluted with further dichloromethanie (50 ml)
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-5594887cc4fb4197b037ae9d57b3f256
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Reaction notes

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