Imidazole → HCID 70574668, compound

HRID 1680493Notes

Reaction equation

HRID 1680493 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][C:13](O)=[O:14])[CH:6]=[C:5]2[CH2:16][C:17]1[NH:18][CH:19]=[CH:20][N:21]=1.[CH3:22][S:23]([NH2:26])(=[O:25])=[O:24].N1C=CN=C1>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][C:13](=[O:14])[NH:26][S:23]([CH3:22])(=[O:25])=[O:24])[CH:6]=[C:5]2[CH2:16][C:17]1[NH:18][CH:19]=[CH:20][N:21]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 72879MethanesulfonamideHCID 70574679HCID 70574679, compound

Product 1

HCID 70574668HCID 70574668, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-bromo-1-(2-carboxyethyl)-3-(1-imidazolylmethyl) indole (0.87 g) and N,N'-carbonyldiimidazole (0.51 g) was heated on a steam bath for 1.5 hours to give a clear melt. Methanesulphonamide (0.47 g) was added and the mixture was heated at 120° C. for 2 hours and then cooled and dissolved in a small volume of ethanol. Some insoluble material was filtered off and the filtrate was evaporated and the residue was chromatographed on silica gel. Elution with chloroform gave initially some impurity. Further elution with a mixture of chloroform and methanol (9:1) gave a mixture of product and imidazole. The product containing fractions were evaporated and the residue was crystallised from a mixture of methanol and ether to give 5-bromo-1-[2-(N-methanesulphonylcarbamoyl)ethyl]-3-(1-imidazolylmethyl)indole (0.31 g,), m.p. 199°-201° C. Found: C, 45.21; H, 4.18; N, 12.95. C16H17BrN4O3S requires: C, 45.18; H, 4.03; N, 13.17%.

Workup

  1. temperaturewas heated on a steam bath for 1.5 hours
  2. customto give a clear melt
  3. temperaturecooled
  4. filtrationSome insoluble material was filtered off
  5. customthe filtrate was evaporated
  6. customthe residue was chromatographed on silica gel
  7. washElution with chloroform
  8. customgave initially some impurity
  9. washFurther elution
  10. additionwith a mixture of chloroform and methanol (9:1)
  11. customgave
  12. additionThe product containing fractions
  13. customwere evaporated
  14. customthe residue was crystallised from a mixture of methanol and ether

Sources & evidence

ORD record
ord-7915e997706a4dadbc1a9a68a1771198
Source dataset
uspto-grants-1981_06
Patent number
US04273782

Reaction notes

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