Tetrahydrofuran → Methyl 2-(aminocarbonothioyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

HRID 631846ノート

反応式

HRID 631846 の反応式
[S-:1][C:2]#[N:3].[NH4+].Cl.[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][NH:15][CH2:14][CH2:13]2)=[O:9].C1COCC1>CCOC(C)=O>[NH2:3][C:2]([N:15]1[CH2:14][CH2:13][C:12]2[C:17](=[CH:18][CH:19]=[C:10]([C:8]([O:7][CH3:6])=[O:9])[CH:11]=2)[CH2:16]1)=[S:1]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 15666Ammonium thiocyanateHCID 42614607Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride

生成物 1

HCID 58147281Methyl 2-(aminocarbonothioyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate収率 100.1%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of ammonium thiocyanate (0.105 g, 1.384 mmol), 6-methoxycarbonyl-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.3 g, 1.3176 mmol) and THF (2 mL) was heated in a CEM microwave reactor for 1 h at 100° C. Upon cooling to room temperature, the reaction mixture was diluted with EtOAc, and washed with H2O, 1 N HCl, saturated aqueous NaHCO3 and brine respectively, dried over anhydrous MgSO4, and concentrated under reduced pressure to afford methyl 2-(aminocarbonothioyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (0.33 g, 47%) as a white solid. LCMS: (FA) ES+251.

後処理

  1. temperatureUpon cooling to room temperature
  2. washwashed with H2O, 1 N HCl, saturated aqueous NaHCO3 and brine respectively
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-babe609544e7486ba413f9cd8ffe4136
出典データセット
uspto-grants-2016_04
特許番号
US09321731B2

反応ノート

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