4-Chlorobenzoyl chloride → 4-Chloro-N-(3-[1,3]dioxolan-2-yl-phenyl)-benzamide

HRID 1486718Notes

Reaction equation

HRID 1486718 reaction equation
[CH2:1]1[O:12][CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=2)[O:3][CH2:2]1.[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>C(OCC)(=O)C>[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([CH:4]3[O:3][CH2:2][CH2:1][O:12]3)[CH:6]=2)=[O:19])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 70203623-(1,3-Dioxolan-2-yl)aniline

Product 1

HCID 867065474-Chloro-N-(3-[1,3]dioxolan-2-yl-phenyl)-benzamideYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 3-aminobenzaldehyde ethylene acetal (10 g, 60.5 mmol) and TEA (7.35 g, 72.6 mmol) in ethyl acetate (100 mL) at 0° C. is treated dropwise with 4-chlorobenzoyl chloride (9.44 mL, 72.6 mmol) during 30 min. The reaction mixture is stirred at RT for 3 h before dilution with EtOAc. The medium is washed twice with sat. aq. NaHCO3 (100 mL) and once with brine (100 mL). The organic layer is dried over MgSO4, filtered and evaporated. The residual oil is triturated with ethyl acetate and the resulting crystalline material is filtered to give the title compound (14.33 g, 78%) as a slightly pink solid; LC-MS B: tR=0.86 min; [M+H]+=304.03.

Workup

  1. washThe medium is washed twice with sat. aq. NaHCO3 (100 mL) and once with brine (100 mL)
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residual oil is triturated with ethyl acetate
  6. filtrationthe resulting crystalline material is filtered

Sources & evidence

ORD record
ord-9d57be9c7c424d10aebaf36ad488450a
Source dataset
uspto-grants-2016_08
Patent number
US09428456B2

Reaction notes

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