Dimethylformamide dimethyl acetal → HCID 86693806, compound

HRID 1754883Notes

Reaction equation

HRID 1754883 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH3:9][C:10]1[CH:16]=[C:15]([C:17]#[C:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:14]([CH3:23])=[CH:13][C:11]=1[NH2:12]>C1(C)C=CC=CC=1>[CH3:5][N:4]([CH3:6])[CH:3]=[N:12][C:11]1[CH:13]=[C:14]([CH3:23])[C:15]([C:17]#[C:18][Si:19]([CH3:21])([CH3:20])[CH3:22])=[CH:16][C:10]=1[CH3:9]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 86693800HCID 86693800, compound2×

Product 1

HCID 86693806HCID 86693806, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

N,N-dimethylformamide dimethyl acetal (5.97 g) and 10 ml of toluene were added to 1.09 g of the 2,5-dimethyl-4-(2-trimethylsilyl-1-ethynyl)aniline (Compound 4-27) produced in Production Example 3, and the mixture was stirred at 110° C. for 9 hours. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1), thereby obtaining 0.56 g of N,N-dimethyl-N′-[2,5-dimethyl-4-(2-trimethylsilyl-1-ethynyl)phenyl]formamidine (Compound 59).

Workup

  1. customproduced in Production Example 3
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-8ae43a229258489c9cfe394de5f16f40
Source dataset
uspto-grants-2015_10
Patent number
US09169276B2

Reaction notes

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