Methylamine → HCID 10741054, compound

HRID 1899096Notes

Reaction equation

HRID 1899096 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.Cl[S:24]([OH:27])(=O)=[O:25].[CH3:28][NH2:29]>O1CCCC1>[CH3:28][NH:29][S:24]([C:10]1[S:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)[CH:11]=1)(=[O:27])=[O:25]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 24638Chlorosulfonic acidHCID 103368732-(4-Fluorophenyl)-3-(4-methylsulfonylphenyl)thiophene

Product 1

HCID 10741054HCID 10741054, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene (1.1 g) was added portionwise to chlorosulfonic acid (1 ml), and the mixture was stirred at ambient temperature for 1 hour. The mixture was added to a mixture of 25% methylamine aqueous solution (20 ml) and tetrahydrofuran (20 ml), and stirred at 0° C. for 1 hour. The reaction mixture was extracted with ethyl acetate, and the extract was washed with water, dried and concentrated. The oily residue (2.4 g) was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1), and then recrystallized from ethanol to give colorless crystals of N-methyl-5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-sulfonamide (1.1 g).

Workup

  1. stirringstirred at 0° C. for 1 hour
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe oily residue (2.4 g) was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (20:1)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-34c7054137cd481cb214312f6f65e969
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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