Dichloromethane → HCID 59838590, compound

HRID 1774046Notes

Reaction equation

HRID 1774046 reaction equation
C(OC([NH:11][N:12]([C:19](=[O:28])[C:20]1[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[CH:21]=1)[C:13]([CH3:18])([CH3:17])[CH2:14][O:15][CH3:16])=O)C1C=CC=CC=1.COC.C(Cl)Cl.[SiH](CC)(CC)CC.CCN(CC)CC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCCCCC.C(OCC)(=O)C>[CH3:16][O:15][CH2:14][C:13]([N:12]([C:19](=[O:28])[C:20]1[CH:21]=[C:22]([CH3:27])[CH:23]=[C:24]([CH3:26])[CH:25]=1)[NH2:11])([CH3:18])[CH3:17]

Participants

8

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 12052TriethylsilaneHCID 66764391methyl ether N'-(3,5-dimethyl-benzoyl)-N'-(2-methoxy-1,1-dimethyl-ethyl)-hydrazinecarboxylic acid benzyl ester

Product 1

HCID 59838590HCID 59838590, compoundYield 80.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing 0.94 g (0.002 mol) of methyl ether N′-(3,5-dimethyl-benzoyl)-N′-(2-methoxy-1,1-dimethyl-ethyl)-hydrazinecarboxylic acid benzyl ester, was added 10 mL of CH2Cl2, 0.87 g of Et3SiH, 0.10 g of palladium acetate, and 1 g of Et3N. The reaction mixture was stirred at room temperature for over 10 hours. More CH2Cl2 (10-20 mL) was added, and the mixture was filtered to remove the palladium. The brown CH2Cl2 solution was treated with MgSO4 and charcoal, then filtered and evaporated. The evaporation yielded 0.87 g of a red, oily solid. TLC indicated the presence of the product; Rf=0.44 in 1:1 ethyl acetate:hexane. The product was purified by chromatography, eluted with 19-20% ethyl acetate/hexane to yield 401 mg (80%) of 3,5-dimethyl-benzoic acid N-(2-methoxy-1,1-dimethyl-ethyl)-hydrazide product. 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.1 (s, 2H), 7.0 (s, 1H), 3.682 (s, 2H), 3.377 (s, 3H), 2.319 (s, 6H), 1.493 (s, 3H).

Workup

  1. filtrationthe mixture was filtered
  2. customto remove the palladium
  3. additionThe brown CH2Cl2 solution was treated with MgSO4 and charcoal
  4. filtrationfiltered
  5. customevaporated
  6. customThe evaporation
  7. customyielded 0.87 g of a red, oily solid
  8. customThe product was purified by chromatography
  9. washeluted with 19-20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ee0c06b6442a42f3bd57599379c97b6c
Source dataset
uspto-grants-2016_02
Patent number
US09255273B2

Reaction notes

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