HCID 58107489, compound → HCID 58107410, compound

HRID 1810183Notes

Reaction equation

HRID 1810183 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-99d0c6f14fe045c1af14ad7a0e74f07c
Source dataset
uspto-grants-2013_01
Patent number
US08362063B2

Reaction notes

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