Toluene → HCID 44474264, compound

HRID 1620806Notes

Reaction equation

HRID 1620806 reaction equation
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].C([O-])(=O)C.[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]

Participants

7

Reactant 4

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

Product 1

HCID 44474264HCID 44474264, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

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) under nitrogen. Acetic acid (5.0-fold, V/W of starting material) was added, followed by 5-tert-butylsulfanyl-2,2-dimethyl-4-oxo-pentanoic acid ethyl ester (1.05 eq) and sodium acetate (2.3 eq), and the reaction mixture was stirred at room temperature for 4 days. Cold water (15.0-fold, V/W of starting material) was then added to the reaction, and the mixture was agitated for 30 minutes. The organic layer was separated, and the aqueous layer was extracted with toluene (2.0-fold, V/W of starting material) to recover additional product. The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated under reduced pressure. A slurry of the crude material was made in methanol (5.0-fold, V/W of starting material), and the mixture was cooled to 0-5° C. for 4 hours. The solid was collected by filtration and washed with cold methanol, and the isolated material was dried under reduced pressure at 28-30° C.

Workup

  1. stirringthe mixture was agitated for 30 minutes
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with toluene (2.0-fold, V/W of starting material)
  4. customto recover additional product
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. temperaturethe mixture was cooled to 0-5° C. for 4 hours
  9. filtrationThe solid was collected by filtration
  10. washwashed with cold methanol
  11. customthe isolated material was dried under reduced pressure at 28-30° C.

Sources & evidence

ORD record
ord-c0d05de1216a468eb2bc946b94ba41bd
Source dataset
uspto-grants-2014_07
Patent number
US08772495B2

Reaction notes

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