Acetone → 1,1-Dimethylethyl 1-methyl-2-(1 methylethylidene)-hydrazinecarboxylate

HRID 1674493Notes

Reaction equation

HRID 1674493 reaction equation
[CH3:1][N:2]([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[NH2:3].[CH3:11][C:12]([CH3:14])=O.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C([O-])(=O)C.[Na+]>C(OCC)C>[CH3:1][N:2]([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[N:3]=[C:12]([CH3:14])[CH3:11]

Participants

6

Reactant 4

HCID 180AcetoneHCID 517045Sodium AcetateHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 37482801-Boc-1-methylhydrazine2×

Product 1

HCID 251049941,1-Dimethylethyl 1-methyl-2-(1 methylethylidene)-hydrazinecarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 1,1-dimethylethyl 1-methylhydrazine carboxylate (179 g) (intermediate 5) in diethyl ether (2 L), at room temperature, acetone (126 ml), glacial acid acetic (7.7 ml) and sodium acetate (1.27 g) were added. After stirring over night, the reaction mixture was quenched with water, the organic phase was dried with sodium sulphate and the solvent evaporated to give the title compound (182.38 g) as a colourless oil.

Workup

  1. customthe reaction mixture was quenched with water
  2. dry with materialthe organic phase was dried with sodium sulphate
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-9ccbd2bd39884e3c838e6c92ea6805e6
Source dataset
uspto-grants-2011_08
Patent number
US08003638B2

Reaction notes

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