Phthaloyl chloride → HCID 1000719, compound

HRID 1889685Notes

Reaction equation

HRID 1889685 reaction equation
[C:1](Cl)(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4](Cl)=[O:5].[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[F:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH:19][C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([NH:19][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([F:13])=[CH:15][CH:16]=2)=[O:5])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6955Phthaloyl chlorideHCID 673264-Fluorobenzylamine

Product 1

HCID 1000719HCID 1000719, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of phthaloyl dichloride (3 g, 15 mmol, 1 eq) in toluene (HPLC grade, 20 mL), cooled to 0° C., was added slowly a solution of 4-fluorobenzylamine (4.62 g, 37 mmol, 2.2 eq) in toluene (5 mL). After stirring at ambient temperature for 24 h, the reaction mixture was concentrated in vacuo to remove toluene. The resultant residue was dissolved in DCM, washed with brine and dried over Na2SO4. The organic layer was evaporated under reduced pressure. Recrystallization from DCM:hexane afforded the desired compound (4.6 g, 82%). 1H NMR (400 MHz, DMSO-d6) δ 9.3 (s, 2H), 9.1 (s, 2H), 8.64 (s, 1H), 7.39-7.34 (m, 4H), 7.17-7.12 (m, 4H), 4.48-4.46 (d, 4H). MS (ESI): 381.2 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customto remove toluene
  3. dissolutionThe resultant residue was dissolved in DCM
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customThe organic layer was evaporated under reduced pressure
  7. customRecrystallization from DCM

Sources & evidence

ORD record
ord-36b2448684f84ea9964bdd05a6bd1535
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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