Ethanol → HCID 54019087, compound

HRID 1824326Notes

Reaction equation

HRID 1824326 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[NH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)(=[O:31])=[O:30])=[CH:24][CH:23]=1.[CH2:38](O)C>C(O)(=O)C>[OH:1][C@@H:2]([CH2:3][NH:19][CH2:20][CH:21]([C:22]1[CH:23]=[CH:24][C:25]([NH:28][S:29]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)(=[O:31])=[O:30])=[CH:26][CH:27]=1)[CH3:38])[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazoleHCID 15281645N-[4-(2-aminoethyl)phenyl]Benzenesulfonamide

Product 1

HCID 54019087HCID 54019087, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Conditions

Temperature
45 °C

Procedure

A stirred mixture of (S)-4-(oxiranylmethoxy)-9H-carbazole (478.5 mg, 2.0 mmol), N-(4-[2-aminoethyl]phenyl)benzenesulfonamide (829.1 mg, 3.0 mmol), acetic acid (1 drop), and ethanol (50 mL) was heated at 45° C. for 16 h with a slow stream of nitrogen bubbling through the reaction mixture. The mixture was cooled and concentrated in vacuo to an amorphous solid. The solid was taken up in ethyl acetate (150 mL) and washed once with 1N HCl (20 mL) and twice with aqueous saturated sodium bicarbonate solution and finally with water. The organic layer was then dried over anhydrous magnesium sulfate, filtered, and concentrated to dryness. The resulting white amorphous product was purified by radial chromatography (Chromatatron) using EtOAc:MeOH (9:1). Concentration of the appropriate fractions and drying under vacuum gave 290 mg (29%) of the desired product as an amorphous white solid. Anal. Calcd. for C29H29N3O4S.0.5 mol H2O: C, 66.39; H, 5.76; N, 8.01. Found: C, 66.49; H, 5.81; N, 7.77.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo to an amorphous solid
  3. washwashed once with 1N HCl (20 mL) and twice with aqueous saturated sodium bicarbonate solution and finally with water
  4. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe resulting white amorphous product was purified by radial chromatography (Chromatatron)
  8. customConcentration of the appropriate fractions and drying under vacuum

Sources & evidence

ORD record
ord-18de2bc0f21447148e08ebd67aab1514
Source dataset
uspto-grants-2006_05
Patent number
US07041684B2

Reaction notes

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