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

HRID 1660337ノート

反応式

HRID 1660337 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 12708194N,N-Dimethyl-N'-[(1,3,4,9-tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)methyl]-urea収率 85.7%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-1e04df1b6bda4c27ac40eeb593c67288
出典データセット
uspto-grants-1981_12
特許番号
US04307234

反応ノート

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