Hydrochloric Acid → N-(1-ethynylcyclohexyl)-4-methanesulfonyl-phenylmethane sulfonamide

HRID 747387Notes

Reaction equation

HRID 747387 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12](Cl)(=[O:14])=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([NH:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)#C.[CH2:25](N(CC)CC)[CH3:26].Cl>O1CCCC1>[C:25]([C:19]1([NH:18][S:12]([CH2:11][C:8]2[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)(=[O:14])=[O:13])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)#[CH:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 21910575EthynylcyclohexylamineHCID 219624184-(Methylsulfonyl)benzenemethanesulfonyl chloride

Product 1

HCID 17973815N-(1-ethynylcyclohexyl)-4-methanesulfonyl-phenylmethane sulfonamideYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Methanesulfonyl-phenylmethanesulfonyl chloride (10.7 g, 40 mmol) in 100 ml dry tetrahydrofuran was added to a solution of ethynylcyclohexylamine (4.93 g, 40 mmol) and triethylamine (6.13 ml, 44 mmol) in dry tetrahydrofuran (100 ml) at 0-5° C. Then the mixture was stirred for 1 hour at room temperature, poured into 0.05 N hydrochloric acid and stirred again. The precipitate was filtered off, washed with water and dried to yield N-(1-ethynylcyclohexyl)-4-methanesulfonyl-phenylmethane sulfonamide (11.7 g, 82%) as a solid. 1H-NMR (CDCl3) δ 7.93 (d, 2 H), 7.65 (d, 2 H), 4.61 (s, 2 H), 4.32 (s, 1 H), 2.75 (s, 1 H), 3.05 (s, 3 H), 2.15 (m, 2 H), 1.63 (m, 7 H), 1.27 (m, 1 H); MS (IS): 354.1 [M−H]−.

Workup

  1. stirringstirred again
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-153cf428ee0340c88f52f8153331525d
Source dataset
uspto-grants-2008_07
Patent number
US07396846B2

Reaction notes

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