Ethanol → HCID 70575333, compound

HRID 1680484Notes

Reaction equation

HRID 1680484 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH2:14][C:15]2[NH:16][CH:17]=[CH:18][N:19]=2)=[C:6]1[CH:20]([CH3:22])[CH3:21])#[N:2].[OH-].[Na+].C([OH:27])C>Cl>[C:1]([CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH2:14][C:15]2[NH:19][CH:18]=[CH:17][N:16]=2)=[C:6]1[CH:20]([CH3:22])[CH3:21])(=[O:27])[NH2:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 70575965HCID 70575965, compound

Product 1

HCID 70575333HCID 70575333, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1-(2-Cyanoethyl)-2-isopropyl-3-(1-imidazolylmethyl)indole (2.0 g) was dissolved in concentrated hydrochloric acid (10 ml) and the solution was allowed to stand for 18 hours at room temperature. It was cautiously basified with dilute sodium hydroxide solution and the mixture was extracted with ethyl acetate (3×25 ml). The combined ethyl acetate extracts were washed with water and dried (Na2SO4). The solvent was evaporated and the residue was chromatographed on silica gel. Elution with a mixture of chloroform and methanol (95:5) gave initially a small amount of impurity followed by pure product. Evaporation of the product containing fraction gave a gum which solidified on trituration with ethanol. The solid was crystallised from ethanol/petrol (b.p. 60°-80° C.) to give 1-(2-carbamoylethyl)-2-isopropyl-3-(1-imidazolylmethyl)indole (1.03 g), m.p. 169°-171° C. Found: C, 69.54; H, 7.25; N, 18.12. C18H22N4O4 requires: C, 69.64; H, 7.14; N, 18.05.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×25 ml)
  2. washThe combined ethyl acetate extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was evaporated
  5. customthe residue was chromatographed on silica gel
  6. washElution
  7. additionwith a mixture of chloroform and methanol (95:5)
  8. customgave initially a small amount of impurity
  9. customEvaporation of the product
  10. additioncontaining fraction
  11. customgave a gum which
  12. customThe solid was crystallised from ethanol/petrol (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-952c5069e8054ffba2ef9c2f2d760f17
Source dataset
uspto-grants-1981_06
Patent number
US04273782

Reaction notes

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