Sodium Hydroxide → HCID 10293154, 화합물

HRID 913185

반응식

HRID 913185 반응식
[N:1]1([CH2:10][C:11]2[O:15][N:14]=[C:13]([CH3:16])[CH:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:17](Cl)(=[O:21])[C:18](Cl)=[O:19].[CH3:23][C:24]1[CH:28]=[C:27]([NH2:29])[S:26][N:25]=1.[OH-].[Na+]>C(OCC)C.O1CCCC1.C(N(CC)CC)C>[CH3:23][C:24]1[CH:28]=[C:27]([NH:29][C:17](=[O:21])[C:18]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:1]([CH2:10][C:11]3[O:15][N:14]=[C:13]([CH3:16])[CH:12]=3)[CH:2]=2)=[O:19])[S:26][N:25]=1

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 323073-Methylisothiazol-5-amineHCID 65578Oxalyl chlorideHCID 11275877HCID 11275877, 화합물

생성물 1

HCID 10293154HCID 10293154, 화합물

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

반응 조건

온도
0 °C

실험 절차

A solution of 5-(1H-1-indolylmethyl)-3-methylisoxazole (212 mg, 1.0 mmol) in 10 mL diethyl ether was added to oxalyl chloride (254 mg, 2.0 mmol) dropwise at 0° C. The reaction mixture was stirred at 0° C. for 3 hours and then the reaction solvent was evaporated. The residue was dissolved in 5 mL tetrahydrofuran and then the 3-methyl-5-isothiazolamine (114 mg, 1.0 mmol) and triethylamine (1 mL) in 10 mL tetrahydrofuran was added dropwise. The mixture was stirred for 10 hours and then 1 N NaOH (4 mL) was added to the reaction flask dropwise. The mixture was extracted three times with a total of 60 mL of tetrahydrofuran, the organic phase was dried using anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuum. The residue was crystallized from methanol. Yield: 0.27 g, 71%.

후처리

  1. customthe reaction solvent was evaporated
  2. dissolutionThe residue was dissolved in 5 mL tetrahydrofuran
  3. stirringThe mixture was stirred for 10 hours
  4. extractionThe mixture was extracted three times with a total of 60 mL of tetrahydrofuran
  5. customthe organic phase was dried
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuum
  8. customThe residue was crystallized from methanol

출처 및 근거

ORD 기록
ord-90f023475c684d8ba878bdf3b848dffe
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026271B2

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