1,1-Dimethylhydrazine → HCID 59202533, compound

HRID 386980Notes

Reaction equation

HRID 386980 reaction equation
[CH3:1][N:2]([CH3:4])[NH2:3].[CH:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[C:9]=1[NH:17][C:18]1[C:19](=O)[CH2:20][CH2:21][CH2:22][CH:23]=1)([CH3:7])[CH3:6]>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:4])/[N:3]=[C:19]1\[CH2:20][CH2:21][CH2:22][CH:23]=[C:18]\1[NH:17][C:9]1[C:10]([CH:14]([CH3:15])[CH3:16])=[CH:11][CH:12]=[CH:13][C:8]=1[CH:5]([CH3:7])[CH3:6]

Participants

5

Reactant 2

HCID 59761,1-DimethylhydrazineHCID 58409382HCID 58409382, compound

Product 1

HCID 59202533HCID 59202533, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent3×

Procedure

Follow a procedure similar to that of Example C except use toluene (12 mL); 1,1-dimethylhydrazine (0.81 mL, 10.6472 mmol); a solution of titanium(IV) chloride (0.2011 g, 1.0600 mol) in toluene (5 mL); stir for 1 hour; then add 2-(2,6-diisopropylphenylamino)cyclohex-2-enone (0.4889 g, 1.8014 mmol, Preparation 3); followed by 1 mL of rinse toluene; stir the resulting reaction mixture overnight; to give after isolation 0.5222 g (92.5%) of the product (K) as a yellow oil containing about 7% of a minor isomeric product.

Workup

  1. stirringstir
  2. customthe resulting reaction mixture overnight

Sources & evidence

ORD record
ord-be36aae991c54647a552388bce82bcdf
Source dataset
uspto-grants-2013_02
Patent number
US08372927B2

Reaction notes

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