Ammonium Chloride → HCID 66844939、化合物

HRID 2064478ノート

反応式

HRID 2064478 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+]>C(O)C.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

A suspension of 2-methyl-5-(3-nitro-phenyl)-thiazole-4-carboxylic acid methyl ester (44.1 mmol) and ammonium chloride (220 mmol) in a mixture of ethanol (100 mL) and water (50 mL) is treated with iron powder (53.0 mmol) and heated to 80° C. After 4 h an additional portion of iron powder (53.0 mmol) is added, the mixture is stirred at 80° C. for 3 h, further iron powder (26.5 mmol) is added and the mixture is again stirred at 80° C. for 3.5 h. The mixture is allowed to reach RT, diluted with DCM and filtered through Celite. The filtrate is concentrated in vacuo and diluted with DCM and sat aqueous NaHCO3 solution. The layers are separated and the organic layer is washed with water, dried over MgSO4 and concentrated in vacuo to give the desired aniline derivative. LC-MS: tR=0.67 min; [M+H]+=249.4.

後処理

  1. stirringthe mixture is again stirred at 80° C. for 3.5 h
  2. customto reach RT
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate is concentrated in vacuo
  5. additiondiluted with DCM
  6. customThe layers are separated
  7. washthe organic layer is washed with water
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-89f3139eb38e42538c8594c90ffd2a29
出典データセット
uspto-grants-2012_10
特許番号
US08288429B2

反応ノート

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