Triethylamine → HCID 86636267, Verbindung

HRID 541825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541825
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[N+:23]([C:26]1[CH:27]=[C:28]([CH2:32][S:33](Cl)(=[O:35])=[O:34])[CH:29]=[CH:30][CH:31]=1)([O-:25])=[O:24]>O1CCCC1>[N+:23]([C:26]1[CH:27]=[C:28]([CH:29]=[CH:30][CH:31]=1)[CH2:32][S:33]([NH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=1)(=[O:35])=[O:34])([O-:25])=[O:24]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 12877220tert-butyl N-(3-aminophenyl)carbamateHCID 13196775(3-Nitrophenyl)methanesulfonyl chloride

Produkt 1

HCID 86636267HCID 86636267, VerbindungAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Into a 1-neck round-bottom flask was added tert-butyl (3-aminophenyl)carbamate (1.0 g, 4.8 mmol) and tetrahydrofuran (20 mL) and triethylamine (1.0 mL, 7.2 mmol). The mixture was cooled in an ice bath and (3-nitrophenyl)methanesulfonyl chloride (1.1 g, 4.8 mmol) was slowly added. The resultant mixture was warmed to rt. The solvent was removed under vacuum and EtOAc and water added. The aqueous phase was extracted again with EtOAc. The organic layers were combined, dried over Na2SO4 and the solvent removed under vacuum to give the desired product (1.94 g, 99%). LCMS for C18H21N3O6S (M-Boc+H)+: m/z=308.0. 1H NMR (400 MHz, DMSO-d6): δ 9.84 (s, 1H), 9.37 (s, 1H), 8.98 (s, 1H), 8.19 (ddd, J=8.1, 2.3, 1.1 Hz, 1H), 8.11 (t, J=1.9 Hz, 1H), 7.71 (dt, J=7.7, 1.3 Hz, 1H), 7.63 (t, J=7.9 Hz, 1H), 7.44 (t, J=2.0 Hz, 1H), 7.15 (t, J=8.0 Hz, 1H), 7.10 (m, 1H), 6.81 (t, J=8.0 Hz, 1H), 6.78 (br, 1H), 6.75 (ddd, J=7.4, 2.2, 1.6 Hz, 1H), 1.46 (s, 9H).

Aufarbeitung

  1. temperatureThe mixture was cooled in an ice bath
  2. customThe solvent was removed under vacuum and EtOAc and water
  3. additionadded
  4. extractionThe aqueous phase was extracted again with EtOAc
  5. dry with materialdried over Na2SO4
  6. customthe solvent removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-25fdb7c1ab134b61a73e2b21d0ddcec9
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871753B2

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