1,3-Bis(1-isocyanato-1-methylethyl)benzene → HCID 23296771, Verbindung

HRID 1954313

Reaktionsgleichung

Reaktionsgleichung von HRID 1954313
[N:1]([C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([CH3:18])([N:15]=[C:16]=[O:17])[CH3:14])[CH:8]=1)([CH3:6])[CH3:5])=[C:2]=[O:3].[CH2:19]([CH:21]([NH:24][OH:25])[CH2:22][CH3:23])[CH3:20]>ClCCl>[C:9]1([C:13]([CH3:18])([NH:15][C:16]([N:24]([OH:25])[CH:21]([CH2:22][CH3:23])[CH2:19][CH3:20])=[O:17])[CH3:14])[CH:10]=[CH:11][CH:12]=[C:7]([C:4]([NH:1][C:2]([N:24]([CH:21]([CH2:22][CH3:23])[CH2:19][CH3:20])[OH:25])=[O:3])([CH3:6])[CH3:5])[CH:8]=1

Komponenten

4

Edukt 2

HCID 177191,3-Bis(1-isocyanato-1-methylethyl)benzeneHCID 19073513N-(pentan-3-yl)hydroxylamine

Produkt 1

HCID 23296771HCID 23296771, VerbindungAusbeute 88,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1,3-Bis(1-isocyanato-1-methylethyl)benzene (2.3 ml, 10 mmol) and dichloromethane (100 ml) was charged with N-(1-ethylpropyl)hydroxylamine (2.2 g, 21.3 mmol). A precipitate formed immediately and the resulting mixture was maintained overnight. The precipitate was recovered by filtration and dried in vacuo to yield 4.0 g of the desired product as a white powder. Recrystallization from N,N-dimethylformamide.backslash.water provided an analytically pure sample: MP: 170.5-172.0° C. ; 1H NMR (300 MHz, DMSO): δ 8.91 (s, 2H), 7.37 (s, 1H), 7.18 (apparent d, J=1.0 Hz, 3H), 6.53 (s, 2H), 3.75-3.65 (m, 2H), 1.57 (s, 12H), 1.51-1.30 (m, 8H), 0.80 (t, J=7.3 Hz, 12 H); 13C NMR (75 MHz, DMSO): δ 159.3, 147.7, 127.1, 122.2, 121.0, 59.5, 54.3, 29.8, 24.4, 11.2; IR (KBr): 3436, 3160, 2963, 2928, 2873, 1632, 1520, 1380, 1361, 1270, 1232, 1160, 790, 702 cm-1 ; Anal. calc'd for C24H42N4O4 : C, 63.97; H, 9.39; N, 12.43. Found: C, 63.81; H, 9.35; N, 12.48.

Aufarbeitung

  1. customA precipitate formed immediately
  2. temperaturethe resulting mixture was maintained overnight
  3. filtrationThe precipitate was recovered by filtration
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ca6986918720497281f46f6ee6848bcc
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06121323

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