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

HRID 2102780노트

반응식

HRID 2102780 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-3a878cd7311a4754a19f1aa0345b618a
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576091B2

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