Sodium Hydroxide → HCID 10293154、化合物

HRID 913185

反応式

HRID 913185 の反応式
[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

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 323073-Methylisothiazol-5-amineHCID 65578Oxalyl chlorideHCID 11275877HCID 11275877、化合物

生成物 1

HCID 10293154HCID 10293154、化合物

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-90f023475c684d8ba878bdf3b848dffe
出典データセット
uspto-grants-2011_09
特許番号
US08026271B2

関連ノート

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