Ammonium Hydroxide → HCID 21290721, compound

HRID 623225Notes

Reaction equation

HRID 623225 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH2:14][O:15][C:16]([CH3:21])([CH3:20])[C:17](O)=[O:18])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[OH-].[NH4+:27]>ClCCl.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH2:14][O:15][C:16]([CH3:21])([CH3:20])[C:17]([NH2:27])=[O:18])=[C:11]([CH3:13])[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 24386Thionyl ChlorideHCID 71321Romazarit

Product 1

HCID 21290721HCID 21290721, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

4.44 g (14.5 mmol) of 2-[[2-(4-chlorophenyl)-4-methyl-5-oxazolyl]methoxy]-2-methylpropionic acid were dissolved in 40 ml of dry dichloromethane and 1 drop of dimethylformamide was added. 1.96 (16 mmol) of thionyl chloride were added and the mixture was heated to reflux for 4 hours. The cooled solution of the resulting acid chloride was added while stirring to 70 ml of aqueous ammonium hydroxide solution (specific gravity 1.880) and crushed ice. After stirring for 16 hours the suspension was extracted with 200 ml of dichloromethane. The organic phase was separated and washed twice with 100 ml of water each time. The organic phase was dried over magnesium sulphate and filtered, and the solvent was then removed by evaporation under reduced pressure. Recrystallization of the crude solid from ethyl acetate gave 2.2 g (49%) of 2-[[2-(4-chlorophenyl)-4-methyl-5-oxazolyl]methoxy]-2-methylpropionamide of melting point 177°-178° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 hours
  3. customcrushed ice
  4. extractionwas extracted with 200 ml of dichloromethane
  5. customThe organic phase was separated
  6. washwashed twice with 100 ml of water each time
  7. dry with materialThe organic phase was dried over magnesium sulphate
  8. filtrationfiltered
  9. customthe solvent was then removed by evaporation under reduced pressure
  10. customRecrystallization of the crude solid from ethyl acetate

Sources & evidence

ORD record
ord-29aae160dbc34613b8596ae803ef38d9
Source dataset
uspto-grants-1988_09
Patent number
US04774253

Reaction notes

Loading…