Dichloromethane → HCID 20461270, compound

HRID 851447Notes

Reaction equation

HRID 851447 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[H][H].[CH2:10]([C:12]1([CH2:31][CH3:32])[O:16][C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2Cl)([CH2:17]OS(C)(=O)=O)[C:14](=[O:30])[O:13]1)[CH3:11].C(Cl)[Cl:34]>CN(C)C=O>[N:3]1([CH2:17][C:15]2([C:23]3[CH:28]=[CH:27][C:26]([Cl:34])=[CH:25][CH:24]=3)[C:14](=[O:30])[O:13][C:12]([CH2:31][CH3:32])([CH2:10][CH3:11])[O:16]2)[CH:7]=[N:6][CH:5]=[N:4]1

Participants

7

Reactant 5

HCID 6344DichloromethaneHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 20461266HCID 20461266, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20461270HCID 20461270, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

With stirring and under nitrogen 5.2 g of sodium hydride (55% dispersion in oil) are added to 50 ml of absolute dimethyl formamide and then 16.6 g of 1,2,4-triazole are added dropwise, whereupon elemental hydrogen escapes. The reaction mixture is heated for 2 hours to 70° C., then cooled to room temperature and a solution of 29 g (0.08 mole) of 2,2-diethyl-4-(chlorophenyl)-4-methanesulfonyloxymethyl-1,3-dioxolan-5-one in 50 ml of dimethyl formamide are added dropwise. The mixture is then heated until the reaction is complete. The reaction solution is cooled and, after addition of 100 ml of ice-water, the mixture is poured into ice-water. The precipitate is isolated by filtration and dissolved in methylene chloride. The methylene chloride solution is washed with water and dried over sodium sulfate and evaporated to dryness to form a resin, which crystallises by addition of a small amount of diethyl ether. The crystals are collected by filtration and washed with petroleum ether. Compound IX has a melting point of 105°-108° C.

Workup

  1. temperatureThe reaction mixture is heated for 2 hours to 70° C.
  2. temperatureThe mixture is then heated until the reaction
  3. temperatureThe reaction solution is cooled
  4. customThe precipitate is isolated by filtration
  5. washThe methylene chloride solution is washed with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customto form a resin, which
  9. customcrystallises by addition of a small amount of diethyl ether
  10. filtrationThe crystals are collected by filtration
  11. washwashed with petroleum ether

Sources & evidence

ORD record
ord-f144ec28167643799a95c82497b313b9
Source dataset
uspto-grants-1983_05
Patent number
US04384879

Reaction notes

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