Ammonium Chloride → HCID 66844939、化合物

HRID 560258ノート

反応式

HRID 560258 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH3:19])[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1)=[O:4].[Cl-].[NH4+]>CCO.O.C(Cl)Cl.[Fe]>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH3:19])[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)=[O:4]

参加物

7

反応物 2

HCID 25517Ammonium ChlorideHCID 668446302-Methyl-5-(3-nitrophenyl)thiazole-4-carboxylic acid methyl ester

生成物 1

HCID 66844939HCID 66844939、化合物

試薬・触媒・溶媒 4

HCID 23925Iron触媒3 回HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

Iron powder (53.7 mmol) is added to a suspension of 2-methyl-5-(3-nitro-phenyl)-thiazole-4-carboxylic acid methyl ester (44.1 mmol) and ammonium chloride (221 mmol) in a mixture of EtOH (100 mL) and water (50 mL). The mixture is stirred at 80° C. for 4 h, iron powder (53.7 mmol) is added and heating is continued for additional 3 h. After addition of a third portion of iron powder (26.8 mmol) the mixture is heated at 80° C. for additional 3 h, cooled to RT, diluted with DCM and filtered through Celite. The residue is washed with DCM and water and the filtrate is concentrated in vacuo. A sat. aq. NaHCO3 solution and DCM are added and the layers are separated. The organic layer is washed with water, dried over MgSO4 and concentrated in vacuo to give a crude product which is used without further purification. LC-MS: tR=0.67 min; [M+H]+=249.4.

後処理

  1. temperatureheating
  2. waitis continued for additional 3 h
  3. temperatureis heated at 80° C. for additional 3 h
  4. temperaturecooled to RT
  5. filtrationfiltered through Celite
  6. washThe residue is washed with DCM and water
  7. concentrationthe filtrate is concentrated in vacuo
  8. additionA sat. aq. NaHCO3 solution and DCM are added
  9. customthe layers are separated
  10. washThe organic layer is washed with water
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ec3392206d194737a2830e8d321bef35
出典データセット
uspto-grants-2011_11
特許番号
US08063099B2

反応ノート

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