Triethylamine → 3-chloro-N-(1-ethynylcyclohexyl)benzenesulfonamide

HRID 1042066Notes

Reaction equation

HRID 1042066 reaction equation
[C:1]([C:3]1([NH2:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)#[CH:2].C(N(CC)CC)C.[Cl:17][C:18]1[CH:19]=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1>C(Cl)Cl>[Cl:17][C:18]1[CH:19]=[C:20]([S:24]([NH:9][C:3]2([C:1]#[CH:2])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 179093-Chlorobenzenesulphonyl chlorideHCID 1216911-Ethynylcyclohexylamine

Product 1

HCID 866249973-chloro-N-(1-ethynylcyclohexyl)benzenesulfonamideYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-ethynylcyclohexanamine (40 mg, 0.32 mmol) in CH2Cl2, was added triethylamine (68 mL, 0.48 mmol), followed by 3-chlorobenzenesulfonyl chloride (68.2 mg, 0.32 mmol). After 30 min, the mixture was partitioned between ethyl acetate and 3N aq. HCl. The organic layer was washed with sat. NaHCO3, brine, dried over Na2SO4, concentrated in vacuuo to give the title compound as a white solid (90 mg, 93% yield).

Workup

  1. customthe mixture was partitioned between ethyl acetate and 3N aq. HCl
  2. washThe organic layer was washed with sat. NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuuo

Sources & evidence

ORD record
ord-2fd02a35fe1947fda4d21a1d596838a9
Source dataset
uspto-grants-2013_10
Patent number
US08557828B2

Reaction notes

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