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

HRID 1162040Notes

Reaction equation

HRID 1162040 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[CH:13]=[C:14]([CH:21]=C)[C:15]2[O:19][CH:18]=[CH:17][C:16]=2[CH:20]=1)(=[O:11])=[O:10].I([O-])(=O)(=O)=[O:24].[Na+].Cl>O1CCOCC1.N1C(C)=CC=CC=1C.O.[Os](=O)(=O)(=O)=O>[CH:21]([C:14]1[C:15]2[O:19][CH:18]=[CH:17][C:16]=2[CH:20]=[C:12]([S:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])(=[O:10])=[O:11])[CH:13]=1)=[O:24]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 66893854N-(2-Methylphenyl)-7-vinyl-1-benzofuran-5-sulfonamide2×

Product 1

HCID 860580667-Formyl-N-(2-methylphenyl)-1-benzofuran-5-sulfonamide

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 79372,6-LutidineSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(2-Methylphenyl)-7-vinyl-1-benzofuran-5-sulfonamide (1.03 g, 3.3 mmol; Intermediate 59) was dissolved in dioxane (30 mL) and 2,6-lutidine (0.8 mL). Osmium tetroxide (84 mg, 0.33 mmol) was added with stirring followed by a solution of sodium periodate (2.82 g, 13.2 mmol) in water (10 mL). After stirring for 90 minutes, 1 M HCl (40 mL) was added followed by water (200 mL). The precipitated product was collected by filtration, washed with water and dried under vacuo. Yield: 0.95 g (91%) of an off white solid.

Workup

  1. stirringAfter stirring for 90 minutes
  2. filtrationThe precipitated product was collected by filtration
  3. washwashed with water
  4. customdried under vacuo

Sources & evidence

ORD record
ord-6bef46d5a8564502a2f1431473312347
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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