Phosgene → HCID 13092005, compound

HRID 544288Notes

Reaction equation

HRID 544288 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([OH:15])[C:10](=[NH:14])[O:11]CC.C(N(CC)CC)C.[C:23](Cl)(Cl)=[O:24]>O1CCCC1>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[O:15][C:23](=[O:24])[NH:11][C:10]1=[O:14]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 13091964HCID 13091964, compound

Product 1

HCID 13092005HCID 13092005, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-(2-chlorophenyl)-1-hydroxymethanecarboximidate hydrochloride (13 g., 52 mmoles) was combined with 350 ml. of tetrahydrofuran and cooled in an ice-water bath. Triethylamine (16.77 g., 0.166 mole) was added and the stirred mixture perfused with phosgene for 45 minutes at 0° C. After an additional 1 hour at the same temperature, the reaction mixture was poured slowly over 1 1. of crushed ice, with isolation and recrystallization from toluene according to Example 3 to yield 5-(2-chlorophenyl)oxazolidine-2,4-dione (7.43 g., 68%; m.p. 106°-108° C.).

Workup

  1. additionthe reaction mixture was poured slowly over 1 1
  2. customof crushed ice, with isolation and recrystallization from toluene according to Example 3

Sources & evidence

ORD record
ord-ac0b12a107c748e3b582107c6bb39f7f
Source dataset
uspto-grants-1984_05
Patent number
US04448971

Reaction notes

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