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

HRID 647591ノート

反応式

HRID 647591 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) δ1.51(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-dd4c25acff1d4716aaa5e2953ab4c3ed
出典データセット
uspto-grants-1983_10
特許番号
US04409224

反応ノート

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