Hydrochloric Acid → HCID 21290687, compound

HRID 623216Notes

Reaction equation

HRID 623216 reaction equation
S(=O)(=O)(O)O.C([NH2:8])=O.[CH2:9]([O:11][CH2:12][C:13]([O:15][CH2:16][C:17](=O)[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)=O)[CH3:10].Cl>O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]2[N:8]=[C:13]([CH2:12][O:11][CH2:9][CH3:10])[O:15][CH:16]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 713FormamideHCID 1118Sulfuric AcidHCID 21290712HCID 21290712, compound

Product 1

HCID 21290687HCID 21290687, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

40 g (0.41 mol) of concentrated sulphuric acid were added dropwise while stirring to 150 g (3.3 mol) of formamide, the temperature of the solution being held below 10° C. by cooling with ice. 50 g (0.2 mol) of (4-chlorobenzoyl)methyl ethoxyacetate were added and the solution was stirred and heated at 140° C. for 2 hours. The mixture was cooled, poured into 2 l of water, acidified to pH 1 by the addition of concentrated hydrochloric acid and extracted once with 500 ml of toluene and then twice with 250 ml of toluene each time. The combined toluene extracts were washed with water, dried over sodium sulphate, filtered and evaporated. The residual syrup was extracted with 700 ml of hot petrol (b.p. 60°-80° C.). The solution was evaporated to dryness and the residue was redissolved in 150 ml of hot petrol (b.p. 40°-60° C.). Upon cooling in acetone/CO2 the product crystallized and was filtered off rapidly and dried to give 21.7 g (47%) of 4-(4-chlorophenyl)-2-ethoxymethyl-oxazole in the form of a soft solid of indeterminate melting point.

Workup

  1. custombeing held below 10° C.
  2. temperatureby cooling with ice
  3. temperatureThe mixture was cooled
  4. extractionextracted once with 500 ml of toluene
  5. washThe combined toluene extracts were washed with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. extractionThe residual syrup was extracted with 700 ml of hot petrol (b.p. 60°-80° C.)
  10. customThe solution was evaporated to dryness
  11. dissolutionthe residue was redissolved in 150 ml of hot petrol (b.p. 40°-60° C.)
  12. temperatureUpon cooling in acetone/CO2 the product
  13. customcrystallized
  14. filtrationwas filtered off rapidly
  15. customdried

Sources & evidence

ORD record
ord-f662796eeb004069b4f3d80d045686a9
Source dataset
uspto-grants-1988_09
Patent number
US04774253

Reaction notes

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