Acetic Acid → 8-Benzyl-1-(3-methyl-phenyl)-1,3,8-triazaspiro[4,5]dec-2-en-4-one

HRID 565599노트

반응식

HRID 565599 반응식
[CH2:1]([N:8]1[CH2:16][CH2:15][C:11]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)([C:12]([NH2:14])=[O:13])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25](O)(=O)C.C(OCC)(OCC)OCC.[OH-].[NH4+]>C1(C)C=CC=CC=1.O>[CH2:1]([N:8]1[CH2:16][CH2:15][C:11]2([N:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=3)[CH:25]=[N:14][C:12]2=[O:13])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 14923Ammonium HydroxideHCID 31214Ethyl orthoformateHCID 211931981-Benzyl-4-(3-methylphenylamino)isonipecotamide

생성물 1

HCID 212683698-Benzyl-1-(3-methyl-phenyl)-1,3,8-triazaspiro[4,5]dec-2-en-4-one

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

To a mixture of 1-benzyl-4-(3-methylphenylamino)-isonipecotamide (4.3 g, 13.5 mmol) and glacial acetic acid (1.0 mL) in toluene (20 mL) heated under reflux, triethyl orthoformate (2.0 g, 13.5 mmol) was added over a period of 3 h using a syringe pump. The resultant mixture was refluxed for 38 h., and treated with a mixture of concentrated ammonium hydroxide (1.3 mL) and water (3.4 mL). The organic extract was isolated, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was subjected to column chromatography on silica gel eluting with 5% methanol in chloroform. Collection and concentration of appropriate fractions provided the title compound.

후처리

  1. temperatureheated
  2. temperatureunder reflux
  3. extractionThe organic extract
  4. customwas isolated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customCollection and concentration of appropriate fractions

출처 및 근거

ORD 기록
ord-ecbf13bea8af42729fc7e6a7265f32be
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172076B2

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