Sulfanilamide → HCID 10471014, compound

HRID 1585064Notes

Reaction equation

HRID 1585064 reaction equation
O1CCO[CH:2]1[CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)=O.[S:17]([NH2:27])(=[O:26])([C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)=[O:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[N:25]([C:22]3[CH:23]=[CH:24][C:19]([S:17]([NH2:27])(=[O:18])=[O:26])=[CH:20][CH:21]=3)[CH:2]=[CH:6][CH:7]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 5333SulfanilamideHCID 6101p-Toluenesulfonic acidHCID 27586963-(1,3-Dioxolan-2-yl)-1-(4-fluorophenyl)-1-propanone

Product 1

HCID 10471014HCID 10471014, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(1,3-dioxolan-2-yl)-1-(4-fluorophenyl)propan-1-one (Example 8, Step 2) (1.6 g, 7.14 mmol), sulfanilamide (1.35 g, 7.86 mmol), p-toluenesulfonic acid (120 mg) and molecular sieves (4 Å, 3 g) in toluene (250 ml) was heated to reflux for 98 hours. The reaction was cooled, filtered and concentrated. The crude brownish solid (3.2 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4) to give 4-[2-(4-fluorophenyl)-1H-pyrrol-1-yl]benzenesulfonamide (920 mg, 40%) as a white solid: mp (DSC) 206° C. Anal Calc'd. for C16H13N2SFO2 ·0.2 H2O: C, 60.06; H, 4.22; N, 8.76; S, 10.02. Found: C, 60.13; H, 4.21; N, 8.61; S, 10.15.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 98 hours
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude brownish solid (3.2 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4)

Sources & evidence

ORD record
ord-127514f990f04c67b2ed74ba725dcf4d
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

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