Potassium Iodide → HCID 22388331, compound

HRID 1072859Notes

Reaction equation

HRID 1072859 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:16][C:17]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:18]=1[CH2:19]Cl.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O>[Cl:16][C:17]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:18]=1[CH2:19][NH:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 72122,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 79336Dimethyl aminoterephthalate

Product 1

HCID 22388331HCID 22388331, compoundYield 42.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

Dimethyl 2-aminoterephthalate (10.45 g), 2,4-dichlorobenzyl chloride (11.74 g), potassium iodide (8.33 g) and potassium carbonate (13.82 g) in a mixed solvent of toluene (50 ml) and water (30 ml) were heated under reflux for 20 hr. After cooling, toluene (50 ml) was added and the precipitated yellow crystals were collected by filtration. The crystals were washed with water and toluene and dried to give the objective compound (7.87 g). The mother liquor was concentrated and crystallized from ethyl acetate to give the second crystals (4.43 g).

Workup

  1. temperatureunder reflux for 20 hr
  2. temperatureAfter cooling
  3. filtrationthe precipitated yellow crystals were collected by filtration
  4. washThe crystals were washed with water and toluene
  5. customdried

Sources & evidence

ORD record
ord-10849149b81c41d892746e578b98939c
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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