Pyridine → 7-Iodo-N-(2-methylphenyl)-1-benzofuran-5-sulfonamide

HRID 1162038Notes

Reaction equation

HRID 1162038 reaction equation
[I:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([S:11](Cl)(=[O:13])=[O:12])[CH:3]=1.[CH3:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18].N1C=CC=CC=1>ClCCl>[I:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([S:11]([NH:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[CH3:15])(=[O:13])=[O:12])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7242O-ToluidineHCID 534029757-Iodobenzofuran-5-sulfonyl chloride2×

Product 1

HCID 668932577-Iodo-N-(2-methylphenyl)-1-benzofuran-5-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Iodo-1-benzofuran-5-sulfonyl chloride (10 g, 29.2 mmol; Intermediate 56) and 2-methyl aniline (3.43 mL, 32.1 mmol) were dissolved in dichloromethane (150 mL) and pyridine (3.53 mL, 43.8 mmol) was added. The solution was stirred overnight and washed with 1 M HCl (2×100 mL), dried over sodium sulfate and evaporated to give the crude solid product that was recrystallized from methanol. Yield: 5.32 g (44%) of a beige solid.

Workup

  1. washwashed with 1 M HCl (2×100 mL)
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customto give the crude solid product that
  5. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-8fb39ae148f54af58d62ade02b9ae0b0
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

Loading…