Hydrochloric Acid → HCID 22254288, compound

HRID 1741501Notes

Reaction equation

HRID 1741501 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl.O1[CH2:14][CH2:13][NH:12]C1=O>ClCCl.O1CCOCC1>[ClH:1].[NH2:12][CH2:13][CH2:14][NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 79323-ChloroanilineHCID 739492-Oxazolidinone

Product 1

HCID 22254288HCID 22254288, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-chloroaniline (30 mL) in 500 mL of dichloromethane at 0° C. was added dropwise a solution of 4 N HCl in 1,4-dioxane (80 mL). The solution was warmed to room temperature, then concentrated to dryness in vacuo to provide a white powder. A mixture of this powder with 2-oxazolidinone (24.6 g) was heated under nitrogen atmosphere at 160° C. for 10 hours, during which the solids melted, and gas evolution was observed. The reaction was allowed to cool, forming the titled compound as a pale brown solid.

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. customto provide a white powder
  3. temperaturewas heated under nitrogen atmosphere at 160° C. for 10 hours, during which the solids
  4. temperatureto cool

Sources & evidence

ORD record
ord-74159066e4a84636b47dec2dde83c9c9
Source dataset
uspto-grants-1999_10
Patent number
US05972984

Reaction notes

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