O-Xylene → HCID 178443375, compound

HRID 265354Notes

Reaction equation

HRID 265354 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH:29](Br)[CH3:30])[C:8]2=[O:32])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[P:33]([O:40][CH2:41][CH3:42])([O:37]CC)[O:34]CC.[C:43]1(C)C(C)=CC=CC=1>>[PH:33](=[O:34])([OH:40])[OH:37].[CH2:30]([CH:29]([CH2:41][CH3:42])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][N:9]1[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]1=[O:32])[CH3:43]

Participants

4

Reactant 3

HCID 7237O-XyleneHCID 31215Triethyl phosphiteHCID 22916448HCID 22916448, compound

Product 1

HCID 178443375HCID 178443375, compound

Procedure

A solution of 1,4,5-triphenyl-3-(6-bromoheptyl)-imidazol-2-one (1.43 g) and triethyl phosphite (2.49 g) in xylene (8 ml) was heated at reflux temperature for 65 hours. The solution was evaporated to an oil and chromatographed on silica gel (ethyl acetate/ethanol). The resulting oil was taken up in diethyl ether, filtered and evaporated to the titled compound as a clear oil (1.15 g; 72%) Found: C, 69.67; H, 7.13; N, 5.43%; C31H37N2O4P; Requires: C, 69.91; H, 7.00; N, 5.26%.

Workup

  1. temperatureat reflux temperature for 65 hours
  2. customThe solution was evaporated to an oil
  3. customchromatographed on silica gel (ethyl acetate/ethanol)
  4. filtrationfiltered
  5. customevaporated to the titled compound as a clear oil (1.15 g; 72%) Found

Sources & evidence

ORD record
ord-e13b1f17c9e44dc7821c750dbd8753d5
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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