Dimethyl aminoterephthalate → Dimethyl 2-isocyanatoterephthalate

HRID 403210

Reaction equation

HRID 403210 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[C:17](Cl)([O:19]C(=O)OC(Cl)(Cl)Cl)Cl>C1(C)C=CC=CC=1>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:11][C:2]=1[N:1]=[C:17]=[O:19]

Participants

4

Reactant 2

HCID 79336Dimethyl aminoterephthalateHCID 94429Triphosgene

Product 1

HCID 25219824Dimethyl 2-isocyanatoterephthalate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dimethyl 2-aminoterephthalate (3.0 g, 14.34 mmol) and triphosgene (5.1 g, 17.22 mmol) were dissolved in toluene. Stirring was carried out at 110° C. for 6 hours under reflux to obtain 2-isocyanato-terephthalic acid dimethyl ester. After evaporating solvent, the compound was dissolved in 1,4-dioxane and triethylamine in vacuum state. After adding cyclohexylamine (2.5 mL, 21.5 mmol), stirring was carried out at 90° C. for 60 hours under reflux. After the reaction was completed, the produced solid was filtered with ether to obtain 1.75 g (37%) of 2-(3-cyclohexyl-ureido)-terephthalic acid dimethyl ester having a urea structure.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-4328eab0b6a74983adbe676a9fc03334
Source dataset
uspto-grants-2014_06
Patent number
US08748422B2

Linked notes

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