Phosgene → HCID 13092014, compound

HRID 544297Notes

Reaction equation

HRID 544297 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH3:18])[C:6]([O:16][CH3:17])=[C:7]([CH:9]([OH:15])[C:10](=[NH:14])[O:11]CC)[CH:8]=1.[C:19](Cl)(Cl)=[O:20].C(N(CC)CC)C>O1CCCC1>[Cl:2][C:3]1[CH:4]=[C:5]([CH3:18])[C:6]([O:16][CH3:17])=[C:7]([CH:9]2[O:15][C:19](=[O:20])[NH:11][C:10]2=[O:14])[CH:8]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 13091976HCID 13091976, compound

Product 1

HCID 13092014HCID 13092014, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By the procedure of Example 9, except that methylene chloride was used in place of chloroform for product extraction following the quench, ethyl 1-(5-chloro-2-methoxy-3-methylphenyl)-1-hydroxymethanecarboximidate hydrochloride (2.5 g., 8.5 mmoles) in 250 ml. of tetrahydrofuran was reacted with phosgene in the presence of triethylamine (2.7 g., 27 mmoles). The product was isolated by pouring the reaction mixture slowly over 1 liter of crushed ice. The aqueous phase was separated and extracted with three portions of methylene chloride. The combined organic phase/extracts was evaporated to solids. The crude product was taken up in 1N sodium hydroxide, extracted with ether, and acidifed with 3N hydrochloric acid to precipitate the desired product (1.81 g., 83%, m.p. 184°-186° C.). Recrystallization from toluene gave purified 5-(5-chloro-2-methoxy-3-methylphenyl)oxazolidine-2,4-dione (1.57 g., 72% overall; m.p. 187°-189° C.).

Workup

  1. extractionBy the procedure of Example 9, except that methylene chloride was used in place of chloroform for product extraction
  2. customThe product was isolated
  3. customThe aqueous phase was separated
  4. extractionextracted with three portions of methylene chloride
  5. customThe combined organic phase/extracts was evaporated to solids
  6. extractionextracted with ether
  7. customto precipitate the desired product (1.81 g., 83%, m.p. 184°-186° C.)
  8. customRecrystallization from toluene
  9. customgave
  10. custompurified 5-(5-chloro-2-methoxy-3-methylphenyl)oxazolidine-2,4-dione (1.57 g., 72% overall; m.p. 187°-189° C.)

Sources & evidence

ORD record
ord-e08881f526524e919c983755884ad317
Source dataset
uspto-grants-1984_05
Patent number
US04448971

Reaction notes

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