Acetic Acid → HCID 67482283, compound

HRID 2402289Notes

Reaction equation

HRID 2402289 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:5]([O:7][C:8](=[O:9])[C:3]=12)=O.[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1.C(O)(=O)C.O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:4]2[C:3]=1[C:8](=[O:9])[N:19]([CH2:18][C:17]1[CH:20]=[CH:21][C:14]([F:13])=[CH:15][CH:16]=1)[C:5]2=[O:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 673264-FluorobenzylamineHCID 695513-Fluorophthalic anhydride

Product 1

HCID 67482283HCID 67482283, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-fluorophthalic anhydride (20 g, 120 mmol) and 4-fluorobenzylamine (20 g, 160 mmol) was stirred in 150 mL toluene. Glacial acetic acid (4 mL) was added dropwise, and the reaction was stirred at 110° C. Water was trapped with a Dean-Stark trap for 16 h. The reaction was cooled to 0° C. Product was isolated by filtration as an off-white solid, after washing with hexane. Obtain the title compound (34.3 g, quant.).

Workup

  1. temperatureThe reaction was cooled to 0° C
  2. customProduct was isolated by filtration as an off-white solid
  3. washafter washing with hexane

Sources & evidence

ORD record
ord-81325a4260a24b58ab914825c0acc0de
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

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