Methanesulfonyl chloride → Flosulide

HRID 354553Notes

Reaction equation

HRID 354553 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19])[C:7](=[O:20])[CH2:6][CH2:5]2.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1>[F:19][C:13]1[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=1[O:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][C:7]2=[O:20])=[CH:3][C:2]=1[N:1]([S:22]([CH3:21])(=[O:24])=[O:23])[S:22]([CH3:21])(=[O:24])=[O:23].[F:19][C:13]1[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=1[O:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][C:7]2=[O:20])=[CH:3][C:2]=1[NH:1][S:22]([CH3:21])(=[O:24])=[O:23]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 12908976HCID 12908976, compound

Product 2

HCID 71246FlosulideHCID 13084200HCID 13084200, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

12.8 g of 5-amino-6-(2,4-difluorophenoxy)-1-indanone in 95 ml of pyridine was combined at 0° C. with 8.3 ml of methanesulfonyl chloride. After 3 hours at 0° C. and 16 hours at 20° C., the mixture was concentrated, the residue taken up in chloroform, the solution washed with 1 N hydrochloric acid, and concentrated. Chromatography of the residue over silica gel with dichloromethane-ethyl acetate yielded 1.2 g of 6-(2,4-difluorophenoxy)-5-bis(methylsulfonyl)amino-1-indanone, mp 190° C. (from toluene) and subsequently 8.9 g of 6-(2,4-difluorophenoxy)-5-methylsulfonylamino-1-indanone, mp 153° C. (from ethanol).

Workup

  1. concentration16 hours at 20° C., the mixture was concentrated
  2. washthe solution washed with 1 N hydrochloric acid
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1f55e8b755b74844b88968236aefa89b
Source dataset
uspto-grants-1983_03
Patent number
US04375479

Reaction notes

Loading…