Methanesulfonyl chloride → N-[6-(2,4-Difluorophenoxy)-2,3-dihydro-1H-inden-5-yl]methanesulfonamide

HRID 354552Notes

Reaction equation

HRID 354552 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][C:6]=1[NH2:14].[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[F:1][C:2]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][C:6]=1[NH:14][S:21]([CH3:20])(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 128870866-(2,4-Difluorophenoxy)-2,3-dihydro-1H-inden-5-amine

Product 1

HCID 133731N-[6-(2,4-Difluorophenoxy)-2,3-dihydro-1H-inden-5-yl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At 0° C., 13.1 g of 6-(2,4-difluorophenoxy)-5-indanylamine in 60 ml of pyridine was combined with 4.0 ml of methanesulfonyl chloride. After 3 hours at 0° C. and 16 hours at 20° C., the mixture was concentrated, the residue was taken up in chloroform, the solution was washed with 1N hydrochloric acid, and concentrated. Recrystallization of the residue from ethanol yielded 8.1 g of N-[6-(2,4-difluorophenoxy)-5-indanyl]methanesulfonamide, mp 85°-87° C.

Workup

  1. customAt 0° C.
  2. concentration16 hours at 20° C., the mixture was concentrated
  3. washthe solution was washed with 1N hydrochloric acid
  4. concentrationconcentrated
  5. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-cfe73a83f2d9490e818be8db5f5d27cf
Source dataset
uspto-grants-1983_03
Patent number
US04375479

Reaction notes

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