Ammonium Chloride → 3-Amino-4-[(3-chloropyrazin-2-yl)thio]benzyl alcohol

HRID 1059293ノート

反応式

HRID 1059293 の反応式
[Cl:1][C:2]1[C:3]([S:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][C:10]=2[N+:17]([O-])=O)=[N:4][CH:5]=[CH:6][N:7]=1.[Cl-].[NH4+]>O1CCCC1.CC(O)C.O.[Fe]>[NH2:17][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:9]=1[S:8][C:3]1[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=1)[CH2:13][OH:14]

参加物

7

反応物 2

HCID 25517Ammonium ChlorideHCID 114379644-[(3-Chloropyrazin-2-yl)thio]-3-nitrobenzyl alcohol

生成物 1

HCID 235641353-Amino-4-[(3-chloropyrazin-2-yl)thio]benzyl alcohol収率 102.2%

試薬・触媒・溶媒 4

HCID 23925Iron触媒HCID 962Water溶媒HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

1.60 g of 4-[(3-chloropyrazin-2-yl)thio]-3-nitrobenzyl alcohol was dissolved in a solvent mixture of tetrahydrofuran (20 ml)/2-propanol (20 ml)/water (7 ml). After adding 0.16 g of ammonium chloride and 1.50 g of iron powder, the resulting mixture was heated under reflux for 30 minutes. Then the reaction mixture was filtered through celite and concentrated under reduced pressure. After adding ethanol, the reaction mixture was concentrated under reduced pressure. Then tetrahydrofuran was added to the residue and the insoluble matters were separated by filtration. After distilling off the solvent under reduced pressure, 1.47 g of the title compound was obtained as yellow crystals.

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. filtrationThen the reaction mixture was filtered through celite and
  4. concentrationconcentrated under reduced pressure
  5. additionAfter adding ethanol
  6. concentrationthe reaction mixture was concentrated under reduced pressure
  7. additionThen tetrahydrofuran was added to the residue
  8. customthe insoluble matters were separated by filtration
  9. distillationAfter distilling off the solvent under reduced pressure

出典と根拠

ORDレコード
ord-9374dddd8b6943478e4aa9e8b249cda0
出典データセット
uspto-grants-2003_02
特許番号
US06518423B1

反応ノート

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