4'-Chloro-5-fluoro-2-hydroxybenzophenone → HCID 178514768, compound

HRID 405000Notes

Reaction equation

HRID 405000 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][S:5]([NH2:8])(=[O:7])=[O:6].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=O)[C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[OH:24])=[CH:12][CH:11]=1>CO>[Cl:9][C:10]1[CH:11]=[CH:12][C:13](/[C:16](=[N:1]\[CH2:2][CH2:3][CH2:4][S:5]([NH2:8])(=[O:7])=[O:6])/[C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[OH:24])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 1128414'-Chloro-5-fluoro-2-hydroxybenzophenoneHCID 13343446HCID 13343446, compound

Product 1

HCID 178514768HCID 178514768, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Amino-1-propanesulfonamide (0.55 g, 4 mmol; from step 4) was added to a solution of 4′-chloro-5-fluoro-2-hydroxy-benzophenone (1 g, 4 mmol) in methanol (50 mL). The reaction mixture was stirred under reflux for 5 h then concentrated under reduced pressure. The residual material was purified by column chromatography (silica gel, dichloromethane:methanol 90:10 then 80:20). The corresponding solid (after removal of solvent) was recrystallized in diethyl ether to afford 3-{[(1E)-(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylene]amino}propane-1-sulfonamide (0.75 g, 51%). 1H NMR (CDCl3, 500 MHz) δ 2.21 (m, 2H), 3.24 (t, J=7.0 Hz, 2H), 3.47 (t, J=7.0H, 2H), 4.63 (bs, 2H), 6.93 (m, 1H), 6.95 (m, 1H), 7.04 (m, 1H), 7.13 (d, J=8.2 Hz, 2H), 7.54 (d, J=8.2 Hz, 2H), 14.71 (s, 1H). ES-MS (369 M-1).

Workup

  1. temperatureunder reflux for 5 h
  2. concentrationthen concentrated under reduced pressure
  3. customThe residual material was purified by column chromatography (silica gel, dichloromethane:methanol 90:10
  4. customThe corresponding solid (after removal of solvent)
  5. customwas recrystallized in diethyl ether

Sources & evidence

ORD record
ord-0c8c505e623e4c1cad06ddcdfa06bf41
Source dataset
uspto-grants-2014_06
Patent number
US08748656B2

Reaction notes

Loading…