N-(5-(phenylamino)penta-2,5-dienylidene)aniline monohydrochloride → 2-[6-anilino-1,3,5-hexatrienyl]-4,6-diiodo-1,3,3-trimethyl-3H-indolium iodide

HRID 579411Notes

Reaction equation

HRID 579411 reaction equation
[I-].[I:2][C:3]1[CH:11]=[C:10]([I:12])[CH:9]=[C:8]2[C:4]=1[C:5]([CH3:16])([CH3:15])[C:6]([CH3:14])=[N+:7]2[CH3:13].Cl.[C:18]1([NH:24][CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=NC2C=CC=CC=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OC(=O)C)(=O)C>[I-:2].[NH:24]([CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=[CH:14][C:6]1[C:5]([CH3:16])([CH3:15])[C:4]2[C:8](=[CH:9][C:10]([I:12])=[CH:11][C:3]=2[I:2])[N+:7]=1[CH3:13])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 73902N-(5-(phenylamino)penta-2,5-dienylidene)aniline monohydrochlorideHCID 866953314,6-diiodo-1,2,3,3-tetramethyl-3H-indolium iodide

Product 1

HCID 866953412-[6-anilino-1,3,5-hexatrienyl]-4,6-diiodo-1,3,3-trimethyl-3H-indolium iodide

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

100 mg (0.18 mmol) of 4,6-diiodo-1,2,3,3-tetramethyl-3H-indolium iodide and 51 mg (0.18 mmol) of N-[5-(phenylamino)-2,4-pentadienylidene]aniline monohydrochloride were stirred in 2 mL of acetic anhydride at 110-120° C. for 15 min. After cooling the product was precipitated with ether, filtered off and washed with ether. Yield: 67 mg (53%). λmax (abs) 483 nm (methanol). This product was used for following step without additional purification.

Workup

  1. temperatureAfter cooling the product
  2. customwas precipitated with ether
  3. filtrationfiltered off
  4. washwashed with ether
  5. customwithout additional purification

Sources & evidence

ORD record
ord-7c92ba9432604588b4247edc7ffd8e9c
Source dataset
uspto-grants-2015_05
Patent number
US09040721B2

Reaction notes

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