Hydrochloric Acid → 4-Nitro-benzylidene-hydantoin

HRID 462190Notes

Reaction equation

HRID 462190 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:12]1[CH2:18][C:16](=[O:17])[NH:15][C:13]1=[O:14].C(CN)O.Cl>O>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[C:18]2[NH:12][C:13](=[O:14])[NH:15][C:16]2=[O:17])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5414-NitrobenzaldehydeHCID 700EthanolamineHCID 10006Hydantoin

Product 1

HCID 46859054-Nitro-benzylidene-hydantoin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of p-nitrobenzaldehyde (2.510 g.) and hydantoin (1.671 g., 1 molar ratio) in water (15 ml) was heated to 70°. Monoethanolamine (1.53 g., 1.5 molar ratio) was added and the mixture was stirred magnetically and heated at 90°-92° (bath temperature) for 41/4 hours. The mixture was cooled in an ice-bath and acidified with HCl. After refrigeration overnight the mixture was filtered, washed with water and dried at 55°/10 mm. The title compound was obtained as a brown solid (3.258 g.), m.p. 252°-253° decomp.

Workup

  1. temperaturewas heated to 70°
  2. temperatureheated at 90°-92° (bath temperature) for 41/4 hours
  3. temperatureThe mixture was cooled in an ice-bath
  4. filtrationAfter refrigeration overnight the mixture was filtered
  5. washwashed with water
  6. customdried at 55°/10 mm

Sources & evidence

ORD record
ord-fc99e0b4f64d4a4ea3391a8997944fde
Source dataset
uspto-grants-1977_12
Patent number
US04065570

Reaction notes

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