Sodium Chloride → 861135-62-8

HRID 2261313Notes

Reaction equation

HRID 2261313 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][OH:6])=[NH:4].[CH3:7][C:8]([CH3:14])([CH3:13])[CH2:9][C:10](Cl)=O.C(N(CC)CC)C.[Cl-].[Na+]>CN(C)C=O>[Cl:1][CH2:2][C:3]1[N:4]=[C:10]([CH2:9][C:8]([CH3:14])([CH3:13])[CH3:7])[O:6][N:5]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 815143,3-Dimethylbutanoyl chlorideHCID 178511097HCID 178511097, compound

Product 1

HCID 43120219861135-62-8Yield 8.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

2.0 g of 2-chloro-N-hydroxyacetoamidine and 2.6 g of 3,3-dimethylbutyryl chloride were dissolved in 30 ml of N,N-dimethylformamide, and 2.05 g of triethylamine was added dropwise under ice-cooling. After completion of the addition, the mixture was stirred at 130° C. for 5 hours and then cooled to room temperature. After aqueous saturated sodium chloride was added, the reaction mixture was extracted with methyl-t-butyl ether. The organic layer was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.28 g of 3-(chloromethyl)-5-(2,2-dimethylpropyl)-1,2,4-oxadiazole.

Workup

  1. temperaturecooling
  2. additionAfter completion of the addition
  3. temperaturecooled to room temperature
  4. extractionthe reaction mixture was extracted with methyl-t-butyl ether
  5. washThe organic layer was washed with aqueous saturated sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7596739d4e3c4a5fbbcfcfd8e256ca8e
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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