Isatoic Anhydride → HCID 20085604, compound

HRID 1608835Notes

Reaction equation

HRID 1608835 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[N:6]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:8][N:9]=1.[C:29]12[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=1)[NH:34]C(=O)O[C:30]2=[O:31]>C(O)C>[NH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:29]=1[C:30]([NH:1][CH2:2][CH2:3][CH2:4][C:5]1[N:6]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:8][N:9]=1)=[O:31]

Participants

4

Reactant 2

HCID 8359Isatoic AnhydrideHCID 20085574HCID 20085574, compound

Product 1

HCID 20085604HCID 20085604, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

The subtitled compound was prepared substantially in accordance with the method detailed in Example 39A using 16.5 g (0.0449 mol) of 2-(3-aminopropyl)-1-tritylimidazole and 7.5 g (O.046 mol) of isatoic anhydride, with the exception that after reducing the organic layer to dryness under reduced pressure to provide a solid the solid was filtered through silica gel using 3000 ml of methylene chloride followed by 4000 ml of a 2% methanol in methylene chloride solution. The resulting filtrate was reduced to dryness under reduced pressure to provide a foamy oil. This oil was dissolved in 1000 ml of boiling ethanol. The resulting solution was then reduced under reduced pressure to approximately 200 ml in volume and then cooled to 0° C. while solids precipitated. These solids were recovered by filtration and washed with ethanol to provide 18.6 g of the desired subtitled intermediate (m.p. 198.5°-207° C.).

Workup

  1. customto provide a solid the solid
  2. filtrationwas filtered through silica gel using 3000 ml of methylene chloride
  3. customto provide a foamy oil
  4. customprecipitated
  5. filtrationThese solids were recovered by filtration
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-803dab2f1a37402892b0daac3d1d5a1a
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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