Isatoic Anhydride → HCID 178507502, compound

HRID 1608833Notes

Reaction equation

HRID 1608833 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1.[C:9]12[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:14]C(=O)O[C:10]2=[O:11]>C(O)C>[NH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=1[C:10]([NH:1][CH2:2][CH2:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)=[O:11]

Participants

4

Reactant 2

HCID 8359Isatoic AnhydrideHCID 178419017HCID 178419017, compound

Product 1

HCID 178507502HCID 178507502, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The subtitled compound was prepared substantially in accordance with the method detailed in Example 6A using 5.55 g (0.05 mol) of 4-(2-aminoethyl)imidazole in 40 ml ethanol and 8.31 g (0.05 mol) of isatoic anhydride with the exception that after removing ethanol from the reaction solution the product was purified using column chromatography (500 ml dichloromethane; 2000 ml 9% methanol in dichloromethane, isocratic eluent). The fractions containing the desired product were combined and reduced to dryness under reduced pressure to provide a solid. This solid was recrystallized from diethyl ether to provide 1.65 g of the desired subtitled compound (m.p. 85°-87° C.).

Workup

  1. customThe subtitled compound was prepared substantially in accordance with the method
  2. customthat after removing ethanol from the reaction solution the product
  3. customwas purified
  4. additionThe fractions containing the desired product
  5. customto provide a solid
  6. customThis solid was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-dcd1f6ec798e41efaf398ec653ce43ce
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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