O-Xylene → HCID 178443374, compound

HRID 1376329Notes

Reaction equation

HRID 1376329 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 (1.47g) 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 dear oil (0.33g; 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 dear oil (0.33g; 19%) Found

Sources & evidence

ORD record
ord-1a69875a095a4dd9881dd1bf5e2c7ace
Source dataset
uspto-grants-1997_09
Patent number
US05663053

Reaction notes

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