Carbon Tetrachloride → HCID 15521323, compound

HRID 1975974Notes

Reaction equation

HRID 1975974 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[CH:7][NH:6][C:5]2=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.[NH2:39][C:40]1[CH:41]=[C:42]2[C:46](=[CH:47][CH:48]=1)[NH:45][CH:44]=[CH:43]2>ClC(Cl)C>[NH:45]1[C:46]2[C:42](=[CH:41][C:40]([NH:39][C:5]3[C:4]4[C:9](=[CH:10][C:11]([O:12][CH3:13])=[C:2]([I:1])[CH:3]=4)[N:8]=[CH:7][N:6]=3)=[CH:48][CH:47]=2)[CH:43]=[CH:44]1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 788675-AminoindoleHCID 135742280HCID 135742280, compound

Product 1

HCID 15521323HCID 15521323, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

In a round bottom flask 6-Iodo-7-methoxy-3H-quinazolin-4-one (500 mg, 1.65 mmol), triphenyl phosphine polymer (2.75 gm, 3 mmol/gm) and carbon tetrachloride (2.53 gm, 16.5 mmol) were combined in 3 mL of dichloroethane and heated at reflux for 5 hours. 5-Aminoindole (686 mg, 1.65 mmol) was added to the mixture and heated at 50° C. overnight. Reaction mixture was concentrated in vacuo and the residue was chromatographed on silica gel 20% MeOH/1% ammonium hydroxide (NH4OH)/CHCl3 to provide 186 mg (28%) of product as a pale yellow solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. customReaction mixture
  4. concentrationwas concentrated in vacuo
  5. customthe residue was chromatographed on silica gel 20% MeOH/1% ammonium hydroxide (NH4OH)/CHCl3

Sources & evidence

ORD record
ord-1bc531a315d54dcba8ed5c135081ae20
Source dataset
uspto-grants-2001_05
Patent number
US06225318B1

Reaction notes

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