Triethylamine → 4-[(2-Nitro-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester

HRID 22875

Reaktionsgleichung

Reaktionsgleichung von HRID 22875
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[C:14]([O:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][CH:21]=1)([CH3:17])([CH3:16])[CH3:15].C(N(CC)CC)C>ClCCl>[C:14]([O:18][C:19](=[O:28])[C:20]1[CH:21]=[CH:22][C:23]([CH2:26][NH:27][S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])=[CH:24][CH:25]=1)([CH3:17])([CH3:15])[CH3:16]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 14514888tert-Butyl 4-(aminomethyl)benzoate

Produkt 1

HCID 697944154-[(2-Nitro-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl esterAusbeute 95,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Nitro-benzenesulfonyl chloride (8.55 g, 38.6 mmol) and 4-aminomethyl-benzoic acid tert-butyl ester (8.0 g, 38.6 mmol) were mixed in 400 mL of dichloromethane. Triethylamine (10.8 mL, 77.2 mmol) was added, and the resulting mixture was stirred at room temperature for 16 hours. The reaction was partitioned between 1M HCl and dichloromethane. The organic layer was dried (magnesium sulfate), filtered, and rotary evaporated to give 14.46 g (95%) of 4-[(2-nitro-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester as an off-white solid. 1H-NMR (CDCl3); δ 8.00 (dd, 1H), 7.84 (m, 3H), 7.67 (m, 2H), 7.27 (dd, 2H), 5.76 (bt, 1H), 4.36 (d, 2H), and 1.57 (s, 9H). MS: M+=392.1 Da Step (2): Synthesis of 4-[(2-Amino-benzenesulfonylamino)-methyl]-benzoic acid tert-butyl ester

Aufarbeitung

  1. customThe reaction was partitioned between 1M HCl and dichloromethane
  2. dry with materialThe organic layer was dried (magnesium sulfate)
  3. filtrationfiltered
  4. customrotary evaporated

Quellen und Nachweise

ORD-Eintrag
ord-4c7eaee1139e429ca701066c340c8244
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849648B2

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