4-Chloroaniline → 1-(4-Chlorophenyl)-3-[1-(3-isopropenylphenyl)-1-methyl-ethyl]urea

HRID 64222

Reaktionsgleichung

Reaktionsgleichung von HRID 64222
[C:1]([C:4]1[CH:5]=[C:6]([CH:13]=[CH:14][CH:15]=1)[C:7]([N:10]=[C:11]=[O:12])([CH3:9])[CH3:8])([CH3:3])=[CH2:2].[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>ClCCl>[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:11]([NH:10][C:7]([C:6]2[CH:13]=[CH:14][CH:15]=[C:4]([C:1]([CH3:3])=[CH2:2])[CH:5]=2)([CH3:9])[CH3:8])=[O:12])=[CH:19][CH:18]=1

Komponenten

4

Edukt 2

HCID 78124-ChloroanilineHCID 6041521-(1-Isocyanato-1-methylethyl)-3-(1-methylethenyl)benzene

Produkt 1

HCID 191683531-(4-Chlorophenyl)-3-[1-(3-isopropenylphenyl)-1-methyl-ethyl]ureaAusbeute 110,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 3-isopropenyl α, α-dimethylbenzyl isocyanate 2 (473 mg, 2.35 mmol) in dichloromethane (6 mL) at 0° C. was added 4-chloroaniline (300 mg, 2.35 mmol) in dichloromethane (3 mL). The reaction was stirred until complete consumption of starting materials. The precipitated product was collected by filtration and washed with dichloromethane to give 5b (852 mg, 80%). mp 234-236° C. Yield 80%; 1H NMR (DMSO-d6, 400 MHz) δ 1.58 (s, 6H), 2.08 (s, 3H), 5.06 (s, 1H), 5.36 (s, 1H), 6.64 (s, 1H), 7.20 (d, J=6.4 Hz, 2H), 7.23-7.32 (m, 5H), 7.47 (s, 1H), 8.55 (s, 1H); 13C NMR (DMSO-d6, 100 MHz) δ 22.24, 30.30, 55.0, 113.06, 119.50, 122.35, 123.69, 124.86, 124.95, 128.65, 129.09, 140.11, 140.73, 143.60, 148.95, 154.53; ESI-HRMS for C9H22N2OCl (M+H)+ calcd. 329.1421. found 329.1418.

Aufarbeitung

  1. filtrationThe precipitated product was collected by filtration
  2. washwashed with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-130c08263bab4fa8a36c2aa83743a947
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447134B2

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