O-Xylene → HCID 178443374, compound

HRID 265353Notes

Reaction equation

HRID 265353 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][CH2:29][CH2:30]Br)[C:8]2=[O:32])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[P:33]([O:42]C(C)C)([O:38]C(C)C)[O:34][CH:35]([CH3:37])[CH3:36].[C:46]1(C)[C:47](C)=CC=C[CH:51]=1>>[PH:33](=[O:34])([OH:42])[OH:38].[CH:35]([CH:30]([CH:46]([CH3:47])[CH3:51])[CH2:29][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])([CH3:37])[CH3:36]

Participants

4

Reactant 3

HCID 7237O-XyleneHCID 8304Triisopropyl phosphiteHCID 229163881,4,5-Triphenyl-3-(7-bromoheptyl)imidazol-2-one

Product 1

HCID 178443374HCID 178443374, compound

Procedure

A solution of 1,4,5-triphenyl-3-(7-bromoheptyl)-imidazol-2-one (1.47 g) and triisopropyl phosphite (3.12 g) in xylene (15 ml) was heated at reflux temperature for 48 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 (0.33 g; 19%) Found: C, 70.02; H, 7.53; N, 5.19%; C34H43N2O4P+1.5% H2O; Requires: C, 69.99; H, 7.60; N, 4.80%.

Workup

  1. temperatureat reflux temperature for 48 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 (0.33 g; 19%) Found

Sources & evidence

ORD record
ord-941fcca0c144480ea9aac74f4ba3db9f
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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