Imidazole → HCID 70576803, compound

HRID 1680476Notes

Reaction equation

HRID 1680476 reaction equation
CN([CH2:4][C:5]1[C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[NH:7][CH:6]=1)C.[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1>C1(C)C(C)=CC=CC=1>[Cl:14][C:11]1[CH:10]=[C:9]2[C:8](=[CH:13][CH:12]=1)[NH:7][CH:6]=[C:5]2[CH2:4][C:16]1[NH:15][CH:19]=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 134914391-(5-Chloro-1H-indol-3-yl)-N,N-dimethylmethanamine

Product 1

HCID 70576803HCID 70576803, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 5-chlorogramine (3.73 g) and imidazole (1.22 g) in xylene (20 ml) was heated under reflux for 3 hours and the cooled. The solid was filtered off, washed with toluene followed by petrol and then crystallised from a mixture of isopropanol and petrol (b.p. 60°-80° C.) to give 5-chloro-3-(1-imidazolylmethyl)indole (3.50 g), m.p. 195°-197° C. Found: C, 62.48; H, 4.31; N, 18.09. C12H10ClN3 requires: C, 62.20; H, 4.35; N, 18.14%.

Workup

  1. temperatureunder reflux for 3 hours
  2. filtrationThe solid was filtered off
  3. washwashed with toluene
  4. customcrystallised from a mixture of isopropanol and petrol (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-5866a1cbb8c44ae5afc865778a42de97
Source dataset
uspto-grants-1981_06
Patent number
US04273782

Reaction notes

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