Triethylamine → 4-chlorophenyl-N-(1-ethynylcyclohexyl)methane-sulfonamide

HRID 1245282Notes

Reaction equation

HRID 1245282 reaction equation
[C:1]([C:4]1([NH:10][S:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)(=O)[CH3:2].ClC1C=CC(CS(Cl)(=O)=O)=CC=1.C(NC1CCCCC1)#C.C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][S:11]([NH:10][C:4]2([C:1]#[CH:2])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]2)(=[O:13])=[O:12])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 227304(4-Chlorophenyl)methanesulfonyl chlorideHCID 11461652N-(1-acetylcyclohexyl)-4-chlorophenyl-methanesulfonamideHCID 21910575Ethynylcyclohexylamine

Product 1

HCID 112899184-chlorophenyl-N-(1-ethynylcyclohexyl)methane-sulfonamideYield 80%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The preparation of N-(1-acetylcyclohexyl)-4-chlorophenyl-methanesulfonamide, shown below, was performed as described in Pestic. Sci. 1993, 39, 185–192. 4-chloro-phenylmethanesulfonyl chloride (1.37 g, 6 mmol) and ethynylcyclohexylamine (0.73 g, 6 mmol) were stirred in tetrahydrofuran (10 mL) with triethylamine (0.9 mL, 6.6 mmol) for several hours at room temperature. The mixture was diluted with ethyl acetate, washed with water, dried (Na2SO4) and evaporated. Recrystallisation from ethanol yielded 4-chlorophenyl-N-(1-ethynylcyclohexyl)methane-sulfonamide (1.5 g, 80%) as a solid.

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-86b5dc3006cc4e979aac2ea7010a15eb
Source dataset
uspto-grants-2006_10
Patent number
US07125840B2

Reaction notes

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