Water → HCID 70574932, compound

HRID 1680475Notes

Reaction equation

HRID 1680475 reaction equation
[OH-].[CH2:2]([N+:9](C)(C)C)[C:3]1C=CC=C[CH:4]=1.[NH:13]1[CH:17]=[CH:16][N:15]=[C:14]1[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1.C(#N)C=C.O>CO.O1CCOCC1>[C:2]([CH:3]([C:20]1[NH:21][C:22]2[C:27]([C:19]=1[CH2:18][C:14]1[NH:15][CH:16]=[CH:17][N:13]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:4])#[N:9]

Participants

7

Reactant 4

HCID 962WaterHCID 7855AcrylonitrileHCID 66854Benzyltrimethylammonium hydroxideHCID 538640233-(1-Imidazolylmethyl) indole

Product 1

HCID 70574932HCID 70574932, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A 40% solution of benzyltrimethylammonium hydroxide in methanol (0.5 ml) was added to a suspension of 3-(1-imidazolylmethyl) indole (1.97 g) in dioxan (25 ml) containing acrylonitrile (2.0 ml) to give a clear solution. The solution was heated to 50°-60° C. for 30 minutes and then allowed to cool and stand overnight at room temperature. It was then poured into water and the mixture was extracted with ethyl acetate (3×50 ml). The combined extracts were washed with water and dried (Na2SO4). Evaporation of the solvent gave 1-cyanoethyl-3-(1-imidazolylmethyl)indole (2.50 g) as an oil.

Workup

  1. customto give a clear solution
  2. temperatureThe solution was heated to 50°-60° C. for 30 minutes
  3. temperatureto cool
  4. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
  5. washThe combined extracts were washed with water
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4bfe630303c64bb3a534d81d42cdd8a3
Source dataset
uspto-grants-1981_06
Patent number
US04273782

Reaction notes

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