Hydrochloric Acid → 7-Formyl-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide

HRID 1162042Notes

Reaction equation

HRID 1162042 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[NH:10][S:11]([C:14]1[CH:15]=[C:16]([CH:23]=C)[C:17]2[O:21][CH:20]=[CH:19][C:18]=2[CH:22]=1)(=[O:13])=[O:12].N1C(C)=CC=CC=1C.I([O-])(=O)(=O)=[O:34].[Na+].Cl>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH:23]([C:16]1[C:17]2[O:21][CH:20]=[CH:19][C:18]=2[CH:22]=[C:14]([S:11]([NH:10][C:4]2[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])(=[O:12])=[O:13])[CH:15]=1)=[O:34]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 66893105N-(2-Methoxy-5-methylphenyl)-7-vinyl-1-benzofuran-5-sulfonamide2×

Product 1

HCID 860580837-Formyl-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamideYield 98.3%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Osmium tetroxide (84 mg, 0.33 mmol) was added to a solution of N-(2-methoxy-5-methylphenyl)-7-vinyl-1-benzofuran-5-sulfonamide (1.25 g, 3.3 mmol; Intermediate 61) and lutidine (0.71 g, 6.6 mmol) in dioxane (30 mL). A solution of sodium periodate (2.82 g, 13.2 mmol) in water (10 mL) was added under stirring. After 90 min, aqueous HCl (2 M; 40 mL) was added to give a clear solution. Addition of water (200 mL) gave a precipitate that was collected by filtration. This material was washed with water and dried to give 1.12 g (88%) of the title product. 1H NMR (400 MHz, CDCl3) δ 2.27 (s, 3H), 3.55 (s, 3H), 6.57 (d, 1H), 6.80-6.85 (m, 1H), 6.92 (d, 1H), 7.02 (br s, 1H), 7.38 (d, 1H), 7.85 (d, 1H), 8.22 (d, 1H), 8.28 (d, 1H), 10.38 (s, 1H).

Workup

  1. customto give a clear solution
  2. customgave a precipitate that
  3. filtrationwas collected by filtration
  4. washThis material was washed with water
  5. customdried

Sources & evidence

ORD record
ord-bfe9f24acd7f4c8c98552a41a7bbf201
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

Loading…