HCID 58107489, compound → HCID 58107410, compound

HRID 1515454Notes

Reaction equation

HRID 1515454 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-a19ed4f21ad747e6a8ec4d2baf2eedff
Source dataset
uspto-grants-2012_07
Patent number
US08222424B2

Reaction notes

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