Diethyl Ether → 2-Amino-4-(3-cyanophenyl)-5-carboethoxythiazole

HRID 1062673ノート

反応式

HRID 1062673 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].[NH2:18][C:19]([NH2:21])=[S:20].C(OCC)C>O1CCCC1>[NH2:21][C:19]1[S:20][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:18]=1

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 2723790ThioureaHCID 22282470Ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate

生成物 1

HCID 222824852-Amino-4-(3-cyanophenyl)-5-carboethoxythiazole収率 102.7%

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 (4.0 g, 13.5 mmol) in 100 mL of tetrahydrofuran was added thiourea (1.03 g, 13.5 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 triturated with ether, taken up in ethyl acetate, washed with saturated aq Na2CO3 and brine, dried (MgSO4) and concentrated in vacuo to yield a solid. Trituration with ethyl ether left the title compound as an off-white solid (3.79 g, 98%).

後処理

  1. temperatureto cool
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was triturated with ether
  4. washwashed with saturated aq Na2CO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto yield a solid

出典と根拠

ORDレコード
ord-d19b10cfcc5e4f20aba60ec8af47cc49
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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