Hydrochloric Acid → HCID 13092027, compound

HRID 647174Notes

Reaction equation

HRID 647174 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[O:14][C:13](=[O:15])[NH:12][C:11]1=[O:16])([O-])=O.[ClH:17]>CO.[Fe]>[ClH:17].[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[O:14][C:13](=[O:15])[NH:12][C:11]1=[O:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 130920255-(2-Nitrophenyl)oxazolidine-2,4-dione

Product 1

HCID 13092027HCID 13092027, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 887MethanolSolvent

Procedure

5-(2-Nitrophenyl)oxazolidine-2,4-dione (5.0 g., 22.5 mmoles) was taken up in a mixture of methanol (11.5 ml.) and conc. hydrochloric acid (12.3 ml.). Powdered iron (3.77 g., 67.5 mmoles) was added over 30 minutes, during which an exothermic reaction brought the temperature to reflux and the mixture became homogeneous. The mixture was cooled to room temperature and stirred for 3 hours. Additional iron powder (1.2 g.) was added and the mixture stirred for 0.5 hour, poured into 100 ml. of water and extracted with three portions of ethyl acetate. The combined ethyl acetate extracts were back washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to a foamed solid. The crude product was taken up in 55 ml. of ethanol, cooled to 0° C., perfused with hydrogen chloride for 10 minutes (crystallization began at this stage), diluted with ether and filtered to recover purified 5-(2-aminophenyl)oxazolidine-2,4-dione hydrochloride [2.52 g., m.p. 205° -209° C. (dec); m/e 192].

Workup

  1. customan exothermic reaction
  2. temperatureto reflux
  3. stirringthe mixture stirred for 0.5 hour
  4. additionpoured into 100 ml
  5. extractionof water and extracted with three portions of ethyl acetate
  6. washThe combined ethyl acetate extracts were back washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo to a foamed solid
  10. temperatureof ethanol, cooled to 0° C.
  11. waitperfused with hydrogen chloride for 10 minutes
  12. custom(crystallization
  13. additiondiluted with ether
  14. filtrationfiltered
  15. customto recover
  16. custompurified 5-(2-aminophenyl)oxazolidine-2,4-dione hydrochloride [2.52 g., m.p. 205° -209° C. (dec); m/e 192]

Sources & evidence

ORD record
ord-5e36099ce0d84a54be54605c38bec4e6
Source dataset
uspto-grants-1983_10
Patent number
US04407811

Reaction notes

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