Toluene → HCID 18940669, compound

HRID 355750Notes

Reaction equation

HRID 355750 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C1(C)C=CC=CC=1.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][C:25]=1[N:31]1[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]1>ClCCl.C(N(CC)CC)C>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:6](=[O:8])[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)=[CH:26][C:25]=1[N:31]1[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 63184-Chlorobenzoic AcidHCID 24386Thionyl ChlorideHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 18940669HCID 18940669, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-Chlorobenzoic acid (350 mg, 2.23 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 (494 mg, 2.23 mmol) in dry dichloromethane (40 ml) was added with triethylamine (2 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 (774 mg, 97%) 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-0f27e790d7054e57aed0b82e403ff4de
Source dataset
uspto-grants-1998_11
Patent number
US05834471

Reaction notes

Loading…