Toluene → HCID 54032034, compound

HRID 1075538Notes

Reaction equation

HRID 1075538 reaction equation
[C:1]1([CH:7]=[CH:8][CH:9]=[CH:10][C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)=O.C1(C)C=CC=CC=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][C:28]=1[N:34]1[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]1>ClCCl.C(N(CC)CC)C>[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:11](=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:29][C:28]=1[N:34]1[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 737775-Phenyl-2,4-pentadienoic acidHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 54032034HCID 54032034, compoundYield 101.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

5-Phenylpenta-2,4-dienoic acid (270 mg, 1.55 mmol) was heated at reflux with thionyl chloride (3 ml) and toluene (40 ml) for 2 h, and then evaporated to dryness under reduced pressure. 4-Methoxy-3-(4-methyl-1-piperazinyl)phenylamine (340 mg, 1.55 mmol) in dry dichloromethane (40 ml) was added with triethylamine (1 ml) and the mixture stirred for 1 h. The solution was partitioned between dichloromethane (40 ml) and saturated aqueous potassium carbonate (40 ml), the organic solution dried (sodium sulphate) and evaporated to dryness under reduced pressure to afford an oil, which was purified by column chromatography (silica, chloroform/methanol 5%) to afford the title compound (595 mg, 100%) which was crystallised from methanol/diethyl ether as the oxalate salt.

Workup

  1. customevaporated to dryness under reduced pressure
  2. customThe solution was partitioned between dichloromethane (40 ml) and saturated aqueous potassium carbonate (40 ml)
  3. dry with materialthe organic solution dried (sodium sulphate)
  4. customevaporated to dryness under reduced pressure
  5. customto afford an oil, which
  6. customwas purified by column chromatography (silica, chloroform/methanol 5%)

Sources & evidence

ORD record
ord-8d856fee9ad34efba26aeef91d32590a
Source dataset
uspto-grants-1999_05
Patent number
US05905080

Reaction notes

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