Hydrochloric Acid → (4-phenyl-1,3-thiazol-2-yl)methanamine

HRID 1397306노트

반응식

HRID 1397306 반응식
Cl.[C:2]1([C:8]2[N:9]=[C:10]([CH2:13][NH:14]C(=O)C3C=CC=CC=3)[S:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.CO>O1CCOCC1>[C:2]1([C:8]2[N:9]=[C:10]([CH2:13][NH2:14])[S:11][CH:12]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 723245HCID 723245, 화합물HCID 21584188Chloroform methanol

생성물 1

HCID 4016236(4-phenyl-1,3-thiazol-2-yl)methanamine수율 77.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

6N HCl (4.5 mL) was added to a solution of N-((4-phenylthiazol-2-yl)methyl)benzamide (150 mg, 0.51 mmol) in dioxane (10 mL) and the reaction mixture was stirred at 100° C. for 24 h (reaction monitored by TLC, eluant CHCl3/MeOH). Reaction mixture was concentrated under reduced pressure and the residue was dissolved in water. The aqueous layer was washed twice with EtOAc. The pH of the aqueous layer was then adjusted to pH ˜9 using 10% NaHCO3 and the organic product was extracted with EtOAc. The organic layer was washed with brine and concentrated under reduced pressure to yield (4-phenylthiazol-2-yl)methanamine (75 mg, yield 77%) as orange colored liquid, which was carried through without further purification. 1H NMR (300 MHz, CDCl3) δ 7.91-7.88 (m, 2H), 7.45-7.40 (m, 3H), 7.36-7.31 (m, 1H), 4.25 (br s, 2H), 3.79-3.75 (m, 1H), 3.68-3.63 (m, 1H). MS (ESI) m/z: Calculated for C10H10N2S: 190.06. found: 191.2 (M+H)+.

후처리

  1. customReaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. washThe aqueous layer was washed twice with EtOAc
  5. extractionthe organic product was extracted with EtOAc
  6. washThe organic layer was washed with brine
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-aa79831c87de449586f75271d309d1ee
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901156B2

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