Water → HCID 178521678, Verbindung

HRID 444685

Reaktionsgleichung

Reaktionsgleichung von HRID 444685
[C:1]12([N:11]=[C:12]=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Cl.[NH2:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18][CH2:17]1.C(N(CC)CC)C.O>CN(C=O)C>[OH:22][C@H:19]1[CH2:20][CH2:21][C@H:16]([NH:15][C:12]([NH:11][C:1]23[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]4)[CH2:2]2)[CH2:8]3)=[O:13])[CH2:17][CH2:18]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 20599951-IsocyanatoadamantaneHCID 178479278HCID 178479278, Verbindung

Produkt 1

HCID 178521678HCID 178521678, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-adamantyl isocyanate (10 g, 56.4 mmol) and trans-4-aminocyclohexanol hydrochloride (10.3 g, 67.7 mmol) in DMF (300 mL) was added triethylamine (6.9 g, 67.7 mmol) at 0° C. The reaction mixture was stirred overnight. The reaction mixture was poured into water, and the resulting precipitates were collected and washed with water. The crude product was recrystallized from methanol/water. Yield: 15.5 g (94% of theory). M.P.: 254° C. 1H NMR (300 MHz, DMSO-d6): δ 5.48 (d. J=9 Hz, 1H), 5.38 (s, 1H), 4.48 (d, J=4.7 Hz, 1H), 3.42-3.28 (m, 1H), 3.28-3.13 (m, 1H), 2.02-1.93 (m, 3H), 1.87-1.68 (m, 9H), 1.63-1.54 (m, 7H), 1.24-0.93 (4H).

Aufarbeitung

  1. customthe resulting precipitates
  2. customwere collected
  3. washwashed with water
  4. customThe crude product was recrystallized from methanol/water

Quellen und Nachweise

ORD-Eintrag
ord-83ab5f6921e04a558c67c436007bb3e0
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476043B2

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