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

HRID 490976

반응식

HRID 490976 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 12744623Methyl 2-amino-5-chloro-3-methylbenzenecarboxylate수율 84.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-26bfaa70e7bc4b96b215343277478660
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528260B2

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