Methylthiourea → 2-(Methylamino)-4-(3-cyanophenyl)-5-carboethoxythiazole

HRID 1062670ノート

反応式

HRID 1062670 の反応式
Br[CH:2]([C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=1)=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:18][NH:19][C:20]([NH2:22])=[S:21]>O1CCCC1>[CH3:18][NH:19][C:20]1[S:21][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=2)[N:22]=1

参加物

4

反応物 2

HCID 2723704MethylthioureaHCID 22282470Ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate

生成物 1

HCID 222824632-(Methylamino)-4-(3-cyanophenyl)-5-carboethoxythiazole収率 73%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

To a solution of ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate (0.65 g, 2.2 mmol) in 20 mL of tetrahydrofuran was added N-methylthiourea (0.20 g, 2.2 mmol). The resulting mixture was stirred at 65° C. for 16 h. The reaction was allowed to cool and the solvent was evaporated in vacuo. The residue was taken up in ethyl acetate, washed with saturated aq NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo to yield a solid. Trituration with hexanes/ethyl ether left the title compound as an off-white solid (0.46 g, 73%). MS (ESI) 288.3 (M+H)+.

後処理

  1. temperatureto cool
  2. customthe solvent was evaporated in vacuo
  3. washwashed with saturated aq NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto yield a solid

出典と根拠

ORDレコード
ord-8d02aa7c04fe4e08bf4cbdbd2d5fb687
出典データセット
uspto-grants-2005_11
特許番号
US06962935B2

反応ノート

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