O-Xylene → HCID 178443375, compound

HRID 1376330Notes

Reaction equation

HRID 1376330 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 dear 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 dear oil (1.15 g; 72%) Found

Sources & evidence

ORD record
ord-913af260fb804cc8bb48cfdf545bf8d4
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Reaction notes

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