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Hydrochloric Acid → N-(2-benzoyl-4-chloro-phenyl)-4-iodo-benzenesulfonamide

HRID 18898
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 18898
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH:17]1[C:22]([S:23](Cl)(=[O:25])=[O:24])=[CH:21][CH:20]=[C:19]([I:27])[CH:18]=1.Cl>N1C=CC=CC=1.C1(C)C=CC=CC=1>[C:4]([C:3]1[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:2]=1[NH:1][S:23]([C:22]1[CH:17]=[CH:18][C:19]([I:27])=[CH:20][CH:21]=1)(=[O:25])=[O:24])(=[O:5])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 73994-Iodobenzenesulfonyl chlorideHCID 128702-Amino-5-chlorobenzophenone

Produkt 1

HCID 10028837N-(2-benzoyl-4-chloro-phenyl)-4-iodo-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittel
HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

To a magnetically stirred solution of 2-amino-5-chlorobenzophenone (1.62 g, 7.0 mmol) in dry pyridine (30 mL) was added dropwise a solution of pipsyl chloride in toluene (12 mL) and the reaction was stirred at ambient temperature. The reaction was added to cold (ice bath) 6M hydrochloric acid with stirring and the mixture was extracted with ethyl acetate (3×50 mL). The extracts were washed with water and with saturated aqueous NaCl. The organic layer was dried (MgSO4), filtered and concentrated to give a crystalline solid. The product was filtered, washed with hexane and dried (vacuum) to get white crystalline solid. 1H NMR (CDCl3) δ 9.63 (br s, 1H, NH), 7,75 (dm, 1H, J=8.8 Hz), 7.62 (tm, 1H, J=7.6 Hz), 7.56 (dm, 1H, J=7.6 Hz), 7.48 (m, 3H), 7.32 (m, 5H). MS: m/z 498.0 (M+1).

Aufarbeitung

  1. stirringwith stirring
  2. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  3. washThe extracts were washed with water and with saturated aqueous NaCl
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crystalline solid
  8. filtrationThe product was filtered
  9. washwashed with hexane
  10. customdried (vacuum)
  11. customto get white crystalline solid

Quellen und Nachweise

ORD-Eintrag
ord-b0a0b1bcdaaa45ae94632dc13858f9ea
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07741519B2

Notizen zur Reaktion

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