Cyclohexylamine → N-Cyclohexyl-5-chloro-2-naphthalenesulfonamide

HRID 725777Notes

Reaction equation

HRID 725777 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13]([S:19](Cl)(=[O:21])=[O:20])=[CH:14]2.C(N(C(C)C)CC)(C)C.ClC1C=CC=C2C=1C=CC=C2S(Cl)(=O)=O>C(Cl)(Cl)Cl>[CH:1]1([NH:7][S:19]([C:13]2[CH:12]=[CH:11][C:10]3[C:15](=[CH:16][CH:17]=[CH:18][C:9]=3[Cl:8])[CH:14]=2)(=[O:20])=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 7965Cyclohexylamine2×HCID 81531DiisopropylethylamineHCID 2210045-Chloronaphthalene-1-sulphonyl chlorideHCID 27357775-Chloronaphthalene-2-sulphonyl chloride

Product 1

HCID 19708732N-Cyclohexyl-5-chloro-2-naphthalenesulfonamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The title compound was prepared from the coupling of cyclohexylamine and 5-chloro-2-naphthalenesulfonyl chloride. Cyclohexylamine (1.0 g, 3.8 mmol) and diisopropyl ethylamine (1.35 ml, 7.7 mmol) were dissolved in 30 ml chloroform. 5-Chloro-1-naphthalenesulfonyl chloride (0.88 m., 7.7 mmol) in 20 ml chloroform was added dropwise to the solution. After stirring overnight, the CHCl3 solution was washed with saturated sodium bicarbonate solution and brine. Drying over magnesium sulfate and evaporation of the CHCl3 followed by recrystallization with isopropyl ether/methanol gave 0.92 g (75% yield) of a yellow solid: mp 133°-134° C.; 1H NMR (CDCl3): 8.48 (d, J=1.8, 1 H, H1), 8.38 (d, J=9.0, 1 H, H3), 8.00 (d, J=9.0, 1 H, H4), 7.88 (d, J=8.3, 1 H, H6), 7.71 (d, J=7.5, 1 H, H8), 7.51 (t, J=7.8, 1 H, H7), 5.07 (d, J=7.7, 1 H, NH), 3.23-3.15 (m, 1 H, NHCH, 1.77-1.72 (m, 2 H, ring H's), 1.61-1.55 (m, 2H, ring H's), 1.51-1.45 (m, 1H, ring H), 1.22-1.10 (m, 6H ring H's); anal. calcd. for C16H18NO2SCl; C, 59.34; H, 5.60; N, 4.33; found: C, 59.27; H, 5.60; N, 4.30.

Workup

  1. washthe CHCl3 solution was washed with saturated sodium bicarbonate solution and brine
  2. dry with materialDrying over magnesium sulfate and evaporation of the CHCl3
  3. customfollowed by recrystallization with isopropyl ether/methanol

Sources & evidence

ORD record
ord-f03f65b779d6433d893954be703db7aa
Source dataset
uspto-grants-1998_01
Patent number
US05707985

Reaction notes

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