Methylthiourea → 2-Methylamino-5,6-dihydro-4H-benzothiazol-7-one

HRID 2102780ノート

反応式

HRID 2102780 の反応式
Br[CH:2]1[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]1=O.[CH3:10][NH:11][C:12]([NH2:14])=[S:13]>N1C=CC=CC=1>[CH3:10][NH:11][C:12]1[S:13][C:2]2[C:7](=[O:8])[CH2:6][CH2:5][CH2:4][C:3]=2[N:14]=1

参加物

4

反応物 2

HCID 2723704MethylthioureaHCID 27704762-Bromocyclohexane-1,3-dione

生成物 1

HCID 34274902-Methylamino-5,6-dihydro-4H-benzothiazol-7-one収率 43%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of 2-bromo-cyclohexane-1,3-dione (8.0 g, 41.9 mmol) and methyl thiourea (3.77 g, 41.9 mmol) in pyridine (63 mL) was stirred at room temperature for 16 h. The reaction mixture was concentrated under vacuum, extracted with CH2Cl2 /10% aq NaCl solution, dried, filtered, and concentrated under vacuum. Crystallization from EtOAc afforded the title compound as yellow crystals (3.26 g, 43%): mp 180-182° C. Anal. RP-HPLC: tR 8.4 min (0-60% MeCN, purity 100%). 1H-NMR (CDCl3): δ 7.90 (s, 1H, NH), 2.99 (s, 3H, CH3), 2.72 (t, 2H, J 6.1, CH2), 2.49 (t, 2H, J 6.1, CH2), 2.10 (qu, 2H, J 6.1, CH2). 13C-NMR (CDCl3): δ 191.0, 176.6, 168.0, 120.0, 37.5, 32.5, 27.7, 23.2. MS: (ESI+) m/z 183.07 (M+H)+.

後処理

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. extractionextracted with CH2Cl2 /10% aq NaCl solution
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customCrystallization from EtOAc

出典と根拠

ORDレコード
ord-3a878cd7311a4754a19f1aa0345b618a
出典データセット
uspto-grants-2009_08
特許番号
US07576091B2

反応ノート

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