Water → HCID 178427236, compound

HRID 1577151Notes

Reaction equation

HRID 1577151 reaction equation
[CH3:1][C:2]1[CH:7]=C(C)[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]=[C:11]1[NH:15][CH2:14][CH2:13][NH:12]1.CC[O:18][C:19]([CH3:21])=[O:20].[NH4+].[OH-].O>C(O)(=O)C.[O-2].[O-2].[O-2].[Cr+6]>[C:19]([C:21]1[CH:1]=[C:2]([CH3:7])[C:3]([N:10]=[C:11]2[NH:12][CH2:13][CH2:14][NH:15]2)=[C:4]([CH3:9])[CH:5]=1)([OH:18])=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 178425511HCID 178425511, compound

Product 1

HCID 178427236HCID 178427236, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 176Acetic AcidSolvent

Procedure

2-(2,4,6-Trimethylphenylimino)imidazolidine (2.03 g) is dissolved in glacial acetic acid (50 ml) and cooled as 5.0 g of chromium trioxide is added in small portions. The solution is then heated to 50° in an oil bath for 4 hours when the reaction is complete as shown by tlc [silica gel, EtOAc/iPA/2 N NH4OH (2:5:1 v/v/v). The mixture is poured into water and ice (500 ml) and the resultant precipitate is filtered and washed with water. Recrystallization from ethyl acetate gives pure product, m.p. 116°-117° C. (1.35 g, 76%).

Workup

  1. additionis added in small portions
  2. temperatureThe solution is then heated to 50° in an oil bath for 4 hours when the reaction
  3. filtrationthe resultant precipitate is filtered
  4. washwashed with water
  5. customRecrystallization from ethyl acetate
  6. customgives pure product, m.p. 116°-117° C. (1.35 g, 76%)

Sources & evidence

ORD record
ord-97ab494f20be4e2cac4ec8ff837ddd71
Source dataset
uspto-grants-1981_09
Patent number
US04287201

Reaction notes

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