Sodium Chloride → HCID 57736280, compound

HRID 2261311Notes

Reaction equation

HRID 2261311 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][OH:6])=[NH:4].[CH3:7][C:8]1([C:11](Cl)=O)[CH2:10][CH2:9]1.C(N(CC)CC)C.[Cl-].[Na+]>CN(C)C=O>[Cl:1][CH2:2][C:3]1[N:4]=[C:7]([C:8]2([CH3:11])[CH2:10][CH2:9]2)[O:6][N:5]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 127899391-Methylcyclopropane-1-carbonyl chlorideHCID 178511097HCID 178511097, compound

Product 1

HCID 57736280HCID 57736280, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

2.75 g of 2-chloro-N-hydroxyacetoamidine and 3.0 g of 1-methylcyclopropanecarbonyl chloride were dissolved in 50 ml of N,N-dimethylformamide, and 2.8 g of triethylamine was added dropwise under ice-cooling. After completion of the addition, the mixture was heated to 130° C., stirred for 6 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 0.97 g of 3-(chloromethyl)-5-(1-methylcyclopropyl)-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-0d965d0ea0364d6fbdb2cd00083b91da
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

Loading…