Phosgene → HCID 13092018, compound

HRID 544299Notes

Reaction equation

HRID 544299 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([CH:8]([O:11][Si](C)(C)C)[C:9]#[N:10])[CH:7]=1.[C:18](Cl)(Cl)=[O:19].[O:22]1CCCC1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([CH:8]2[O:11][C:18](=[O:19])[NH:10][C:9]2=[O:22])[CH:7]=1

Participants

4

Reactant 3

HCID 6371PhosgeneHCID 8028TetrahydrofuranHCID 20459921HCID 20459921, compound

Product 1

HCID 13092018HCID 13092018, compound

Procedure

By the procedure of Example 3, 2-(5-bromo-2-methoxyphenyl)-2-trimethylsiloxyethanenitrile (16 g., 0.049 mole) in 320 ml. of tetrahydrofuran was reacted with phosgene. After stirring 16 hours at room temperature, the reaction was quenched into 1 liter of crushed ice and extracted with two 500 ml. portions of ethyl acetate. The combined ethyl acetate extracts were back washed with two 200 ml. portions of brine, dried over anhydrous magnesium sulfate, filtered and evaporated to solids. The solids were recrystallized from toluene to yield purified 5-(5-bromo-2-methoxyphenyl) oxazolidine-2,4-dione (10.7 g., m.p. 166°-167° C.).

Workup

  1. customthe reaction was quenched into 1 liter of crushed ice
  2. extractionextracted with two 500 ml
  3. washThe combined ethyl acetate extracts were back washed with two 200 ml
  4. dry with materialportions of brine, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to solids
  7. customThe solids were recrystallized from toluene
  8. customto yield
  9. custompurified 5-(5-bromo-2-methoxyphenyl) oxazolidine-2,4-dione (10.7 g., m.p. 166°-167° C.)

Sources & evidence

ORD record
ord-4b73fa29e3cb4041b1cd01c23c533420
Source dataset
uspto-grants-1984_05
Patent number
US04448971

Reaction notes

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