Sodium Iodide → HCID 86737805, compound

HRID 1680488Notes

Reaction equation

HRID 1680488 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1.[H-].[Na+].[I-].[Na+].Br[CH2:21][CH2:22][CH2:23][N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34].[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]/[C:38]([OH:40])=[O:39]>CN(C)C=O.C(OCC)(=O)C>[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]/[C:38]([OH:40])=[O:39].[C:25]1(=[O:34])[N:24]([CH2:23][CH2:22][CH2:21][N:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7]([CH2:6][C:2]3[NH:3][CH:4]=[CH:5][N:1]=3)=[CH:8]2)[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]12

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 444972Fumaric AcidHCID 538640233-(1-Imidazolylmethyl) indole

Product 1

HCID 86737805HCID 86737805, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

3-(1-Imidazolylmethyl)indole (3.94 g) was dissolved in N,N-dimethylformamide (50 ml) and the solution was treated with sodium hydride (1.00 g of 50% dispersion in oil) as described in Example 44. To the solution of the anion at 0° C. was added sodium iodide (3.0 g) and N-(3-bromopropyl)phthalimide (5.36 g) over 10 minutes. The mixture was then stirred at room temperature for 20 hours and evaporated to dryness. The residue was chromatographed on silica gel. The column was first eluted with petrol (b.p. 40°-60° C.) to remove mineral oil and then with chloroform to remove the product. The chloroform eluate was evaporated to give a viscous gum which was pure enough for further reaction. A portion was dissolved in ethyl acetate and the solution was treated with an excess of fumaric acid in ethyl acetate. The solid was filtered off and crystallised from ethyl acetate containing a trace of ethanol to give 1-(3-phthalimidopropyl)-3-(1-imidazolylmethyl)indole fumarate, m.p. 166°-167° C. Found: C, 64.56; H, 4.78; N, 11.09. C23H20N4O2.C4H4O4 requires: C, 64.79; H, 4.83; N, 11.20.

Workup

  1. customevaporated to dryness
  2. customThe residue was chromatographed on silica gel
  3. washThe column was first eluted with petrol (b.p. 40°-60° C.)
  4. customto remove mineral oil
  5. customwith chloroform to remove the product
  6. customThe chloroform eluate was evaporated
  7. customto give a viscous gum which
  8. customwas pure enough for further reaction
  9. filtrationThe solid was filtered off
  10. customcrystallised from ethyl acetate containing a trace of ethanol

Sources & evidence

ORD record
ord-511fbc7cf3a545af846b023947d256c2
Source dataset
uspto-grants-1981_06
Patent number
US04273782

Reaction notes

Loading…