N,N,N'-Trimethyl-N'-(6-nitro-benzothiazol-2-yl)ethane-1,2-diamine → N2-(2-Dimethylamino-ethyl)-N2-methyl-benzothiazole-2,6-diamine

HRID 1174907

反応式

HRID 1174907 の反応式
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]([CH3:18])[C:6]1[S:7][C:8]2[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:9]=2[N:10]=1.[H][H]>[Pd].CCO.C1COCC1>[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]([CH3:18])[C:6]1[S:7][C:8]2[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:9]=2[N:10]=1

参加物

6

反応物 2

HCID 57771682N,N,N'-Trimethyl-N'-(6-nitro-benzothiazol-2-yl)ethane-1,2-diamineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 55226563N2-(2-Dimethylamino-ethyl)-N2-methyl-benzothiazole-2,6-diamine収率 80%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Combine N,N,N′-Trimethyl-N′-(6-nitro-benzothiazol-2-yl)ethane-1,2-diamine (5.79 g, 20.6 mmol) and 5% palladium on carbon (5.02 g) in EtOH (200 mL) and THF (25 mL). Shake on a Parr shaker at 60 psi of hydrogen at room temperature for 18 h. Filter the reaction mixture through filter paper, wash with EtOH (50 mL), and concentrate in vacuo to afford the crude title compound (4.1 g, 80%). The crude product was carried on as is. 1H NMR (400 MHz, DMSO-d6): δ 7.10 (d, 1H, J=8.4 Hz), 6.86 (d, 1H, J=1.8 Hz), 6.52 (dd, 1H, J=8.4, 2.2 Hz), 4.80 (br s, 2H), 3.51 (t, 2H, J=6.6 Hz), 3.04 (s, 3H), 2.48 (m, 2H), 2.18 (s, 6H).

後処理

  1. filtrationFilter the reaction mixture
  2. filtrationthrough filter paper
  3. washwash with EtOH (50 mL)
  4. concentrationconcentrate in vacuo

出典と根拠

ORDレコード
ord-9bad5bb8fc5448a8aeec4eb3d64681ad
出典データセット
uspto-grants-2010_11
特許番号
US07838543B2

関連ノート

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