Water → Methyl 2-amino-5-chloro-3-methylbenzenecarboxylate

HRID 490976

反応式

HRID 490976 の反応式
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].S(Cl)([Cl:16])(=O)=O.O.[OH-].[Na+]>C(#N)C>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[C:9]([Cl:16])[CH:10]=[C:11]([CH3:12])[C:2]=1[NH2:1]

参加物

6

反応物 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24648Sulfuryl chlorideHCID 2763406Methyl 3-methylanthranilate

生成物 1

HCID 12744623Methyl 2-amino-5-chloro-3-methylbenzenecarboxylate収率 84.8%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
50 °C

実験手順

The solution prepared in Step A (195 g, 475 mmol) was diluted with acetonitrile (50 mL), and heated to 50° C. Then a solution of sulfuryl chloride (70.6 g, 523 mmol) in acetonitrile (100 mL) was added over 3.25 h at 50-55° C. Immediately after completion of the addition, the mixture was cooled to 5° C., water (150 g) was added, and the pH of the solution was adjusted to 6.0 by slow addition of 50% aqueous sodium hydroxide (103 g). After stirring for 10 minutes at this temperature, the organic layer was separated, and the aqueous layer was extracted with acetonitrile (50 mL). The organic layers were combined, dried (MgSO4), and partially evaporated to a weight of 193.7 g. Quantitative HPLC of this solution showed 41.5 wt % of the title compound (80.4 g, 84.8% yield).

後処理

  1. additionImmediately after completion of the addition
  2. temperaturethe mixture was cooled to 5° C.
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with acetonitrile (50 mL)
  5. dry with materialdried (MgSO4)
  6. custompartially evaporated to a weight of 193.7 g

出典と根拠

ORDレコード
ord-26bfaa70e7bc4b96b215343277478660
出典データセット
uspto-grants-2009_05
特許番号
US07528260B2

関連ノート

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