Triethylamine → N-(4-(methylsulfonyl)phenyl)cyclopentanecarboxamide

HRID 1363744Notes

Reaction equation

HRID 1363744 reaction equation
Cl.[CH3:2][S:3]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)(=[O:5])=[O:4].CCN(CC)CC.[CH:20]1([C:25](Cl)=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]1>CCOCC.CCOC(C)=O>[CH3:2][S:3]([C:6]1[CH:12]=[CH:11][C:9]([NH:10][C:25]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:26])=[CH:8][CH:7]=1)(=[O:4])=[O:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 27351804-(Methylsulfonyl)aniline hydrochloride

Product 1

HCID 4786080N-(4-(methylsulfonyl)phenyl)cyclopentanecarboxamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-(Methanesulfonyl)aniline hydrochloride (19 mmol) suspended in 25 mL of Et2O was added Et3N (48 mmol) and then a solution cyclopentanecarbonyl chloride (19 mmol) in 25 mL of Et2O was added dropwise during in 10 min. The reaction mixture was stirred for 3 h at RT and then diluted with EtOAc (100 mL) washed with 1N aq HCl, water and aq sat NaHCO3. The organic phase was dried and concentrated in vacuo to give crude cyclopentanecarboxylic acid (4-methanesulfonyl-phenyl)-amide which was used without further purification.

Workup

  1. washwashed with 1N aq HCl, water
  2. customThe organic phase was dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3559f714a7e04c3c8cc2a2b39ec926af
Source dataset
uspto-grants-2011_02
Patent number
US07884210B2

Reaction notes

Loading…