Hydrochloric Acid → 2,4-Imidazolidinedione, 5-[(2-chlorophenyl)methylene]-

HRID 597373Notes

Reaction equation

HRID 597373 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH:10]1[CH2:16][C:14](=[O:15])[NH:13][C:11]1=[O:12].C(CN)O.Cl>O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:16]1[NH:10][C:11](=[O:12])[NH:13][C:14]1=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 69962-ChlorobenzaldehydeHCID 10006Hydantoin

Product 1

HCID 28878212,4-Imidazolidinedione, 5-[(2-chlorophenyl)methylene]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of o-chlorobenzaldehyde (2.50 g.) and hydantoin (1.78 g., 1 molar ratio) was treated with water (15 ml) and heated to 70°. Monoethanolamine (1.63 g., 1.5 molar ratio) was added and the mixture was stirred magnetically at 90°-92° (bath temperature) for 4.25 hours. The mixture was cooled in an ice-bath, acidified with concentrated HCl, refrigerated overnight, filtered, washed with water and dried at 55°/10 mm. The title compound was obtained as a pinkish solid (2.63 g.), m.p. 266°-270° decomp.

Workup

  1. temperatureheated to 70°
  2. temperatureThe mixture was cooled in an ice-bath
  3. filtrationfiltered
  4. washwashed with water
  5. customdried at 55°/10 mm

Sources & evidence

ORD record
ord-e23cb373379a4ce8b6c5f1d95e81c58c
Source dataset
uspto-grants-1977_03
Patent number
US04013770

Reaction notes

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