Phosgene → HCID 13092008, compound

HRID 544290Notes

Reaction equation

HRID 544290 reaction equation
[C:1](Cl)(Cl)=[O:2].Cl.[F:6][C:7]1[CH:8]=[C:9]([CH:13]([OH:19])[C:14](=[NH:18])[O:15]CC)[CH:10]=[CH:11][CH:12]=1>C1(C)C=CC=CC=1>[F:6][C:7]1[CH:8]=[C:9]([CH:13]2[O:19][C:1](=[O:2])[NH:15][C:14]2=[O:18])[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 13091970HCID 13091970, compound

Product 1

HCID 13092008HCID 13092008, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

By the procedure of Example 3, except that a reaction time of 16 hours at room temperature was employed following the cold perfusion with phosgene and the product was extracted into methylene chloride following quench over crushed ice, ethyl 1-(3-fluorophenyl)-1-hydroxymethanecarboximidate hydrochloride (16 g., 0.068 mole) was converted to toluene recrystallized 5-(3-fluorophenyl)oxazolidine-2,4-dione (7.51 g., 56%; m.p. 147°-149° C.).

Workup

  1. customexcept that a reaction time of 16 hours
  2. customat room temperature
  3. extractionthe product was extracted into methylene chloride following
  4. customquench
  5. customrecrystallized 5-(3-fluorophenyl)oxazolidine-2,4-dione (7.51 g., 56%; m.p. 147°-149° C.)

Sources & evidence

ORD record
ord-c5abd8b763fc437f97eecf58f46aa707
Source dataset
uspto-grants-1984_05
Patent number
US04448971

Reaction notes

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