1,2-Dichloroethane → HCID 7733132, compound

HRID 533718Notes

Reaction equation

HRID 533718 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([O-:8])=O)=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[F:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1>CN(C=O)C.O>[F:28][C:29]1[CH:35]=[CH:34][C:32]([NH:33][C:6]([C:5]2[CH:4]=[CH:3][C:2]([C:1]([O:12][CH3:13])=[O:11])=[CH:10][CH:9]=2)=[O:8])=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 97314-FluoroanilineHCID 757711-HydroxybenzotriazoleHCID 36144541,4-Benzenedicarboxylic acid, methyl ester

Product 1

HCID 7733132HCID 7733132, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of mono-methyl terephthalate (2.0 g, 11.1 mmol) in DMF (10 mL) was added EDC (2.48 g, 13.3 mmol), HOBt (1.80 g, 13.3 mmol), and 4-fluoroaniline (1.48 g, 13.3 mmol). The reaction was stirred at room temperature for 72 h. The reaction was diluted with water (80 mL) and isolated methyl 4-(4-fluorophenylcarbamoyl)benzoate (3.00 g, 98%) as a white precipitate by vacuum filtration. 1H-nmr (400 MHz, CDCl3) δ 8.18 (d, J=8 Hz, 2H), 7.95 (d, J=8 Hz, 2H), 7.82 (br s, 1H), 7.66-7.59 (m, 2H), 7.15-7.07 (m, 2H), 3.99 (s, 3H); MS (ESI) m/z 273.9.

Sources & evidence

ORD record
ord-e21836ac34c44f9299c537a5d686302f
Source dataset
uspto-grants-2014_10
Patent number
US08853392B2

Reaction notes

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