HCID 58107489, compound → HCID 58107410, compound

HRID 873655Notes

Reaction equation

HRID 873655 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([N:16]([CH2:20]C=C)[CH2:17][CH:18]=[CH2:19])=[CH:12][CH:11]=2)[OH:9])=[CH:4][C:3]=1[S:23]([NH2:26])(=[O:25])=[O:24]>C(Cl)(Cl)Cl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl.ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:17][CH:18]=[CH:19][CH2:20]3)=[CH:12][CH:11]=2)[OH:9])=[CH:4][C:3]=1[S:23]([NH2:26])(=[O:24])=[O:25]

Participants

5

Reactant 1

HCID 58107489HCID 58107489, compound

Product 1

HCID 58107410HCID 58107410, compoundYield 76.7%

Reagents, catalysts & solvents 3

HCID 178479819HCID 178479819, compoundCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 100 mg of 2-chloro-5-((4-diallylamino-phenyl)-hydroxy-methyl)-benzenesulfonamide (0.25 mmol, 1 equivalent) in 5 mL of chloroform is degassed with argon for 5 minutes, then 5 mg of Grubb's catalyst (0.005 mmol, 2% mmol) is added. The reaction mixture is stirred at room temperature for 1 h, then diluted with dichloromethane, filtered through Celite, and a pad of silica gel, then concentrated in vacuo to give 70 mg of the title compound which is carried forward without further purification.

Workup

  1. filtrationfiltered through Celite
  2. concentrationa pad of silica gel, then concentrated in vacuo

Sources & evidence

ORD record
ord-0aea5faee53541148c1ceaa608046ddb
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

Loading…