Chloride → HCID 22923047, compound

HRID 2257485Notes

Reaction equation

HRID 2257485 reaction equation
C[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=O)[CH:3]=1.P(Cl)(Cl)([Cl:21])=O.[CH3:24][N:25]([CH:27]=O)[CH3:26].[Cl-].ClC1C=C(C)C2C(=CC=CC=2)[N+]=1C1C=CC=CC=1.[Cl-].CN([CH:52]([SH:54])C)C>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl-:21].[CH3:24][N:25]([CH3:26])[CH2:27][CH2:52][S:54][C:4]1[CH:3]=[CH:2][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N+:5]=1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

9

Reactant 6

HCID 312ChlorideHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 2691834-methyl-1-phenylquinolin-2(1h)-oneHCID 11630674HCID 11630674, compoundHCID 19374211HCID 19374211, compound

Product 1

HCID 22923047HCID 22923047, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

The 1,2-dihydro-4-methyl-1-phenyl-2-quinolone is heated at reflux with 1.3 equivalents of phosphorus oxychloride and 1 equivalent of DMF in toluene for one hour to generate the 2-chloro-4-methyl-1-phenylquinolinium chloride (3). The chloride is then stirred in the corresponding dimethylaminoethanethiol in methylene chloride to produce the corresponding 2-dimethylaminoethylthio-1-phenylquinolinium chloride. This is then reacted with one equivalent each of the 2-(2-anilinovinyl)-3-methyl-benzoxazolium tosylate, triethylamine and acetic anhydride to generate the corresponding trimethine derivative.

Sources & evidence

ORD record
ord-9b092ceeacbb47fbb40b308db8c0a358
Source dataset
uspto-grants-1997_08
Patent number
US05658751

Reaction notes

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