Phosgene → HCID 13091999, compound

HRID 434810Notes

Reaction equation

HRID 434810 reaction equation
Cl.[OH:2][CH:3]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])[C:4](=[NH:8])[O:5]CC.C(N(CC)CC)C.[C:24](Cl)(Cl)=[O:25]>O1CCCC1>[CH3:16][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH:3]1[O:2][C:24](=[O:25])[NH:5][C:4]1=[O:8]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 13091954HCID 13091954, compound

Product 1

HCID 13091999HCID 13091999, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-hydroxy-1-(2-methoxyphenyl)methanecarboximidate hydrochloride (18 g., 0.073 mole) was suspended in 500 ml. of tetrahydrofuran, cooled to 0°-5° C., and triethylamine (23.6 g., 0.234 mole) was added. The stirred reaction mixture was perfused with phosgene for 30 minutes. Stirring at 0°-5° C. was continued for 1 hour. The reaction mixture was slowly poured over 1 l. of crushed ice and product extracted into three portions of chloroform. The combined chloroform extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to solids. The residue was recrystallized from toluene to yield 5-(2-methoxyphenyl)oxazolidine-2,4-dione (6.4 g., 42%; m.p. 175°-177° C.; m/e 207). A second drop (3.7 g., 24%, m.p. 175°-177° C.) was obtained from the toluene mother liquor.

Workup

  1. customThe stirred reaction mixture
  2. additionThe reaction mixture was slowly poured over 1 l
  3. extractionof crushed ice and product extracted into three portions of chloroform
  4. washThe combined chloroform extracts were washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to solids
  8. customThe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-c5217645313440788aae7fa2a49630fb
Source dataset
uspto-grants-1983_08
Patent number
US04399296

Reaction notes

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