Pyridine → 3-(1-Oxo-4-(thiophen-2-ylsulfonylimino)-1,4-dihydronaphthalen-2-ylamino)-benzoic acid

HRID 1258389Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258389
CN1C(S[C:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)/[C:10](=[N:19]/[S:20]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)(=[O:22])=[O:21])/[CH:9]=2)=NN=N1.[NH2:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32]([OH:34])=[O:33].N1C=CC=CC=1>C1COCC1.C(OCC)(=O)C>[O:18]=[C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[N:19][S:20]([C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)(=[O:22])=[O:21])[CH:9]=[C:8]1[NH:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][CH:37]=1)[C:32]([OH:34])=[O:33]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 74193-Aminobenzoic AcidHCID 46907997(NE)-N-[3-(1-methyltetrazol-5-yl)sulfanyl-4-oxonaphthalen-1-ylidene]thiophene-2-sulfonamide

Produkt 1

HCID 11841343-(1-Oxo-4-(thiophen-2-ylsulfonylimino)-1,4-dihydronaphthalen-2-ylamino)-benzoic acidAusbeute 91,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

33.8 mg (E)-N-(3-(1-methyl-1H-tetrazol-5-ylthio)-4-oxonaphthalen-1(4H)-ylidene)thiophene-2-sulfonamide (12a) was dissolved in 3 ml THF, to which was added 13.7 mg 3-aminobenzoic acid. The resulting orange solution was stirred at r.t. for 30 min and 0.2 ml THF solution containing 1 eq. pyridine was added. The reaction was continued for 30 min. The mixture was diluted to 50 ml with ethyl acetate and washed with 0.5 N NaHSO4 solution, water and brine. Dried over Na2SO4, the organic phase was filtered and the filtrate was concentrated. The residue was washed with dichloromethylene/hexane (1:1) affording the title compound 32.5 mg (74.2%) as a red solid, m.p.: 230° C. (dec.).

Aufarbeitung

  1. additionwas added
  2. waitThe reaction was continued for 30 min
  3. washwashed with 0.5 N NaHSO4 solution, water and brine
  4. dry with materialDried over Na2SO4
  5. filtrationthe organic phase was filtered
  6. concentrationthe filtrate was concentrated
  7. washThe residue was washed with dichloromethylene/hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3e2608faab7042ddad527098bd63f473
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466157B2

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