Ethyl chloroformate → HCID 13093540, compound

HRID 434847Notes

Reaction equation

HRID 434847 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH:10]1[O:14][C:13](=[O:15])[NH:12][C:11]1=[O:16].[Na].Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH:10]1[O:14][C:13](=[O:15])[N:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11]1=[O:16]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 70501533HCID 70501533, compound

Product 1

HCID 13093540HCID 13093540, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Anhydrous sodium 5-(2-chloro-6-methoxyphenyl)oxazolidine-2,4-dione (542 mg., 2.06 moles) from Example 119 and ethyl chloroformate (291 mg., 2.68 mmoles) were combined with 20 ml. of toluene and the mixture refluxed for 3 hours, cooled to room temperature, stirred for a further 16 hours, and evaporated to solids (415 mg.). The solids were recrystallized from toluene to yield purified 5-(2-chloro-6-methoxyphenyl)-3-ethoxycarbonyloxazolidine-2,4-dione. (212 mg., m.p. 196°-200° C.).

Workup

  1. customevaporated to solids (415 mg.)
  2. customThe solids were recrystallized from toluene
  3. customto yield
  4. custompurified 5-(2-chloro-6-methoxyphenyl)-3-ethoxycarbonyloxazolidine-2,4-dione

Sources & evidence

ORD record
ord-ca424f9342924fa69da28964e69faab0
Source dataset
uspto-grants-1983_08
Patent number
US04399296

Reaction notes

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