2-Chlorobenzenesulfonyl chloride → HCID 86584800, compound

HRID 325043Notes

Reaction equation

HRID 325043 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][O:22][C:23]2[CH:24]=[C:25]([NH:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:26]=[C:27]([CH3:29])[CH:28]=2)=[CH:16][CH:15]=1)#[N:13].C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:30]([CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:25]1[CH:26]=[C:27]([CH3:29])[CH:28]=[C:23]([O:22][CH2:21][CH2:20][C:17]2[CH:18]=[CH:19][C:14]([C:12]#[N:13])=[CH:15][CH:16]=2)[CH:24]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 761872-Chlorobenzenesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 86584801HCID 86584801, compound

Product 1

HCID 86584800HCID 86584800, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Chlorobenzenesulfonyl chloride (0.225 g; 1.06 mmol) was added to a cold solution (ice:water temperature) of 3-[2-(4-cyanophenyl)ethoxy]-5-methyl-phenylaminoacetic acid, ethyl ester (0.30 g; 0.88 mmol; from step (i) above) in pyridine (10 mL). After 2 hours stirring the temperature was allowed to rise to ambient. After 4 hours at this temperature more 2-chloro-benzenesulfonyl chloride (0.056 g; 0.26 mmol) was added and the mixture was left overnight. The mixture was then poured into aqueous saturated NaHCO3 and extracted twice with Et2O. The combined ether phases where washed with HCl/aq (2M), H2O and brine, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by flash chromatography (SiO2; EtOAc:heptane (1:3)) to give 0.28 g (62%) of the sub-title compound.

Workup

  1. waitthe mixture was left overnight
  2. extractionextracted twice with Et2O
  3. washThe combined ether phases where washed with HCl/aq (2M), H2O and brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by flash chromatography (SiO2; EtOAc:heptane (1:3))

Sources & evidence

ORD record
ord-0b7a0c4e7c8147acb4d8af2c92ba8d43
Source dataset
uspto-grants-2001_04
Patent number
US06221898B1

Reaction notes

Loading…