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

HRID 657683Notes

Reaction equation

HRID 657683 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>>[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

4

Reactant 3

HCID 8471TriethylamineHCID 179093-Chlorobenzenesulphonyl chlorideHCID 1216911-Ethynylcyclohexylamine

Product 1

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

Procedure

To a solution of 1-ethynylcyclohexanamine (40 mg, 0.32 mmol) in CH2C2 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-faf2e8ae388e4df18476949278ec6e9c
Source dataset
uspto-grants-2011_12
Patent number
US08076344B2

Reaction notes

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