Toluene → HCID 44474264, 화합물

HRID 2366092노트

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HRID 2366092 반응식
Cl.[Br:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)N)=[CH:5][CH:4]=1.C1(C)C=CC=CC=1.[CH2:27]([O:29][C:30](=[O:43])[C:31]([CH3:42])([CH3:41])[CH2:32][C:33](=O)[CH2:34][S:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH3:28].CC([O-])=O.[Na+]>O.C(O)(=O)C>[CH2:27]([O:29][C:30](=[O:43])[C:31]([CH3:42])([CH3:41])[CH2:32][C:33]1[N:8]([CH2:7][C:6]2[CH:18]=[CH:19][C:3]([Br:2])=[CH:4][CH:5]=2)[C:10]2[C:15]([C:34]=1[S:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH3:28]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 517045Sodium AcetateHCID 3576811Ethyl 5-(tert-butylsulfanyl)-2,2-dimethyl-4-oxopentanoateHCID 19041688N-(p-Bromobenzyl)-N-(4-methoxyphenyl)hydrazine hydrochloride

생성물 1

HCID 44474264HCID 44474264, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

N-(4-Bromo-benzyl)-N-(4-methoxy-phenyl)-hydrazine hydrochloride (1.0 eq) was added to a reaction flask containing toluene (10.0-fold, V/W of starting material). To this reaction mixture was added acetic acid (5.0-fold, V/W of starting material), followed by 5-tert-butylsulfanyl-2,2-dimethyl-4-oxo-pentanoic acid ethyl ester (1.05 eq) and NaOAc (2.3 eq). The reaction mixture was agitated at room temperature for about 4 days after which cold water (15.0-fold, V/W of starting material) was added to the reaction and stirred for about 30 minutes. The organic layer was collected and the aqueous layer washed with toluene to recover additional product. The organic portions were collected and washed with water and saturated brine solution. The organic layer was subsequently dried over Na2SO4 and concentrated under reduced pressure. A slurry of collected compound was made with methanol (5.0-fold, V/W of starting material) at 0-5° C. for about 4 hours. The solid was collected and washed with cold methanol. Any remaining solvent was removed by drying under reduced pressure.

후처리

  1. additionwas added to the reaction
  2. customThe organic layer was collected
  3. washthe aqueous layer washed with toluene
  4. customto recover additional product
  5. customThe organic portions were collected
  6. washwashed with water and saturated brine solution
  7. dry with materialThe organic layer was subsequently dried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. waitA slurry of collected compound was made with methanol (5.0-fold, V/W of starting material) at 0-5° C. for about 4 hours
  10. customThe solid was collected
  11. washwashed with cold methanol
  12. customAny remaining solvent was removed
  13. customby drying under reduced pressure

출처 및 근거

ORD 기록
ord-a111155d8a804b4cb611df29ff339947
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697730B2

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