Phosgene → HCID 13092000, compound

HRID 434811Notes

Reaction equation

HRID 434811 reaction equation
Cl.[OH:2][CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:16][CH3:17])[C:4](=[NH:8])[O:5]CC.[C:18](Cl)(Cl)=[O:19]>>[CH2:16]([O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH:3]1[O:2][C:18](=[O:19])[NH:5][C:4]1=[O:8])[CH3:17]

Participants

3

Reactant 2

HCID 6371PhosgeneHCID 13091956HCID 13091956, compound

Product 1

HCID 13092000HCID 13092000, compoundYield 70%

Procedure

Ethyl 1-hydroxy-1-(2-ethoxyphenyl)methanecarboximidate hydrochloride (20 g.) was reacted with phosgene according to the procedure of Example 3. To isolate the product, the reaction mixture was evaporated to dryness and the solid residue partitioned between 500 ml. of water and 500 ml. of chloroform. The aqueous phase was washed with two fresh portions of chloroform. The combined chloroform phase and washes was dried over anhydrous magnesium sulfate, filtered, evaporated to solids and recrystallized from toluene to yield 5-(2-ethoxyphenyl)oxazolidine-2,4-dione (11.9 g., 70%; m.p. 165°-167° C., m/e 221)

Workup

  1. customTo isolate the product
  2. customthe reaction mixture was evaporated to dryness
  3. customthe solid residue partitioned between 500 ml
  4. washThe aqueous phase was washed with two fresh portions of chloroform
  5. dry with materialThe combined chloroform phase and washes was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to solids
  8. customrecrystallized from toluene

Sources & evidence

ORD record
ord-e88a90c16d5546c09e223db5d9176656
Source dataset
uspto-grants-1983_08
Patent number
US04399296

Reaction notes

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