Dimethylcarbamoyl Chloride → N,N-Dimethyl-N'-[(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-urea

HRID 1660337Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1660337
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].[CH3:7][C:8]1([CH2:21][NH2:22])[C:13]2[NH:14][C:15]3[C:20]([C:12]=2[CH2:11][CH2:10][O:9]1)=[CH:19][CH:18]=[CH:17][CH:16]=3.C(N(CC)CC)C.O1CCCC1>C(OCC)C>[CH3:1][N:2]([CH3:6])[C:3]([NH:22][CH2:21][C:8]1([CH3:7])[C:13]2[NH:14][C:15]3[C:20]([C:12]=2[CH2:11][CH2:10][O:9]1)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:4]

Komponenten

6

Edukt 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 127081811,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-methanamine

Produkt 1

HCID 12708194N,N-Dimethyl-N'-[(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-ureaAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Dimethylcarbamic chloride (3.95 g) is added to a solution at 0° C. of 1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indole-1-methanamine (7.9 g, described in Example 3), triethylamine (3.7 g) and tetrahydrofuran (200 ml) over a period of 5 minutes. The mixture is stirred at 0° to 5° C. for 30 minutes and at 25° C. for 18 hours. Diethyl ether (200 ml) is added, the mixture is filtered and the filtrate is evaporated. The residue is crystallized from diethyl ether to obtain the title compound (9.0 g); mp 153°-155° C.; ir (CHCl3) 3450-3250 and 1635 cm-1 ; nmr (CDCl3) δ 1.51 (s) and 2.69 (m).

Aufarbeitung

  1. filtrationthe mixture is filtered
  2. customthe filtrate is evaporated
  3. customThe residue is crystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1e04df1b6bda4c27ac40eeb593c67288
Quelldatensatz
uspto-grants-1981_12
Patentnummer
US04307234

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