Isopropyl iodide → Methyl 3-amino-2-methyl-6-(1-methylethylsulphenyl)-benzoate

HRID 266528ノート

反応式

HRID 266528 の反応式
[NH2:1][C:2]1[C:3]([CH3:15])=[C:4]([C:9](SC#N)=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[S-2:16].[Na+].[Na+].I[CH:20]([CH3:22])[CH3:21]>C(O)C.O>[NH2:1][C:2]1[C:3]([CH3:15])=[C:4]([C:9]([S:16][CH:20]([CH3:22])[CH3:21])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

参加物

6

反応物 3

HCID 6362Isopropyl iodideHCID 14804Sodium SulfideHCID 14801188Methyl 3-amino-2-methyl-6-thiocyanatobenzoate

生成物 1

HCID 54177219Methyl 3-amino-2-methyl-6-(1-methylethylsulphenyl)-benzoate収率 75.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
5 °C

実験手順

A suspension of methyl 3-amino-2-methyl-6-thiocyanatobenzoate (22.2 g) in ethanol was added to a solution of sodium sulphide (26.6 g) in water. The resultant mixture was stirred at room temperature for 1 hour and then cooled to 5° C. 2-Iodopropane (19.36 g) was added and the mixture was allowed to warm to room temperature and stirred for 2 hours. It was evaporated to dryness and the residue was suspended in aqueous sodium chloride solution and extracted with dichloromethane. The organic layer was dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give methyl 3-amino-2-methyl-6-(1-methylethylsulphenyl)benzoate (18 g) as a yellow oil NMR(CDCl3) 1.2(d,6H) 2.0(s,3H) 3.0(m, 1H) 3.8(bs,2H) 3.9(s, 1H) 6.5(d, 1H) 7.0(d, 1H).

後処理

  1. temperatureto warm to room temperature
  2. customIt was evaporated to dryness
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

出典と根拠

ORDレコード
ord-351fc97011b0471bb2bcb5843ff1e216
出典データセット
uspto-grants-1997_07
特許番号
US05650533

反応ノート

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