Butyl 4-aminobenzoate → 4-[3-(Naphthalene-2-carbonyl)-thioureido]-benzoic acid butyl ester

HRID 901887

Reaktionsgleichung

Reaktionsgleichung von HRID 901887
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](Cl)=[O:12].[S-:14][C:15]#[N:16].[NH4+].[NH2:18][C:19]1[CH:31]=[CH:30][C:22]([C:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:24])=[CH:21][CH:20]=1>CC(C)=O>[CH2:26]([O:25][C:23](=[O:24])[C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:15]([NH:16][C:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[O:12])=[S:14])=[CH:31][CH:30]=1)[CH2:27][CH2:28][CH3:29]

Komponenten

5

Edukt 3

HCID 2482Butyl 4-aminobenzoateHCID 15666Ammonium thiocyanateHCID 752462-Naphthoyl chloride

Produkt 1

HCID 103412944-[3-(Naphthalene-2-carbonyl)-thioureido]-benzoic acid butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

2-Naphthoyl chloride (190 mg, 1 mmol) is added to a solution of ammonium thiocyanate (200 mg, about 3 mmol) in acetone (5 ml) and stirred at room temperature for 1 hour. Butyl 4-aminobenzoate (180 mg, 0.93 mmol) is added to the reaction mixture. Stirring is continued overnight at room temperature. The solid, which forms is filtered and washed with water (2×5 ml) followed by acetone/hexane (3:1) (2×10 ml) and dried. The product (140 mg) is characterized by NMR (Bruker, 300 MHz) and MS. 1H NMR (300 MHz, CDCl3) δ (Ppm): 12.9 (s, 1H), 9.27 (1H), 8.43 (s, 1H), 8.11 (d, 2H, J=6.0), 7.99 (d, 2H, J=6.0), 7.91 (m, 4H), 7.65 (m, 2H), 4.34 (t, 2H, J=6.6 Hz), 1.81-1.72 (m, 2H), 1.55-1.43 (m, 2H), 0.99 (t, 3H, J=7.3 Hz). MS (APCI) m/z 407 [M+H]+.

Aufarbeitung

  1. stirringStirring
  2. waitis continued overnight at room temperature
  3. filtrationThe solid, which forms is filtered
  4. washwashed with water (2×5 ml)
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-41a3d059c69c4b369ea492075aa7fa4c
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365068B2

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