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

HRID 1397306ノート

反応式

HRID 1397306 の反応式
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

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 723245HCID 723245、化合物HCID 21584188Chloroform methanol

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-aa79831c87de449586f75271d309d1ee
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

反応ノート

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