Hydrochloric Acid → HCID 13936991, compound

HRID 979515Notes

Reaction equation

HRID 979515 reaction equation
[NH2:1][C:2]([NH:4][C@H:5]([C:17]([OH:19])=O)[CH2:6][C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:16])=[O:3].ClC1C=CC=C([N+]([O-])=O)C=1CCl.Cl>O>[Cl:16][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]([N+:13]([O-:15])=[O:14])[C:7]=1[CH2:6][CH:5]1[NH:4][C:2](=[O:3])[NH:1][C:17]1=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 202004981-Chloro-2-(chloromethyl)-3-nitrobenzeneHCID 53771615HCID 53771615, compound

Product 1

HCID 13936991HCID 13936991, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of DL-N-(aminocarbonyl)-2-chloro-6-nitrophenylalanine (6.15 g, 21 mmol) prepared from 2-chloro-6-nitrobenzyl chloride according to steps 1, 2 and 3 above, concentrated hydrochloric acid (70 mL) and water (70 mL) was heated on a steam bath. After 45 minutes, the mixture was cooled, filtered and the solid washed with water and dried in air to give 5-[(2-chloro-6-nitrophenyl)methyl]-2,4imidazolidinedione (4.90 g, 85%), which was used without further purification. An analytical sample was prepared by dissolving a sample of the crude material (0.6 g) in boiling ethanol (30 mL) and adding ether to precipitate pure material (0.48 g). m.p. 210°-212° C. (dec). Spectral data were in accord with the assigned structure.

Workup

  1. temperaturethe mixture was cooled
  2. filtrationfiltered
  3. washthe solid washed with water
  4. customdried in air

Sources & evidence

ORD record
ord-f9f93c763c754fdd8973ee40b809abc0
Source dataset
uspto-grants-1987_05
Patent number
US04668686

Reaction notes

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