Hydrochloric Acid → HCID 18314487、化合物

HRID 1274592ノート

反応式

HRID 1274592 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]=2[CH:18]=1.CN(C)[C:21]1[O:22][C:23](=[O:31])[CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[N:26]=1.[C:33](=O)([O-])[O-].[K+].[K+].IC.Cl>C(O)(=O)C.CN(C)C=O.C(Cl)Cl.C(OCC)(=O)C>[CH3:33][N:26]1[C:25]([C:27]([F:30])([F:29])[F:28])=[CH:24][C:23](=[O:31])[N:1]([C:2]2[CH:3]=[CH:4][C:5]3[S:9][N:8]=[C:7]([C:10]([CH3:17])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]=3[CH:18]=2)[C:21]1=[O:22]

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-oneHCID 18314476HCID 18314476、化合物

生成物 1

HCID 18314487HCID 18314487、化合物

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of ethyl 5-amino-α,α-dimethyl-1,2-benzisothiazole-3-acetate (0.546 g, 2.06 mmol) and 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one (0.430 g, 2.06 mmol) in acetic acid is refluxed for 4.5 hours, concentrated in vacuo, and diluted with saturated sodium hydrogen carbonate solution. The resultant aqueous mixture is extracted with methylene chloride. The combined organic extracts are washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a brown foam. A solution of the foam in N,N-dimethylformamide is treated with potassium carbonate (0.312 g, 2.25 mmol), stirred for one hour, treated with iodomethane (0.420 mL, 6.70 mmol), stirred overnight at room temperature, and poured into an ice-water mixture containing 20 mL of concentrated hydrochloric acid. The resultant aqueous-mixture is extracted with methylene chloride. The combined organic extracts are washed sequentially with 10% hydrochloric acid, water, saturated sodium hydrogen carbonate solution and water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a brown oil. Column chromatography of the oil using silica gel and a 33% ethyl acetate in methylene chloride solution affords a pink foam which is recrystallized from ethanol to give the title product as pink crystals, mp 164-167° C.

後処理

  1. temperatureis refluxed for 4.5 hours
  2. concentrationconcentrated in vacuo
  3. additiondiluted with saturated sodium hydrogen carbonate solution
  4. extractionThe resultant aqueous mixture is extracted with methylene chloride
  5. washThe combined organic extracts are washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain a brown foam
  9. stirringstirred overnight at room temperature
  10. extractionThe resultant aqueous-mixture is extracted with methylene chloride
  11. washThe combined organic extracts are washed sequentially with 10% hydrochloric acid, water, saturated sodium hydrogen carbonate solution and water
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated in vacuo
  14. customto obtain a brown oil
  15. customis recrystallized from ethanol

出典と根拠

ORDレコード
ord-795b3d96714d41d09a471357d17e8e7d
出典データセット
uspto-grants-2000_12
特許番号
US06156700

反応ノート

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