N,N'-Dimethylethylenediamine → 2-chloro-N-(4-(5-methyl-2-phenyloxazol-4-yl)phenyl)benzamide

HRID 1951586Notes

Reaction equation

HRID 1951586 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH2:12])=[O:11].Br[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:25]=[C:26]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:27][C:28]=2[CH3:29])=[CH:20][CH:19]=1.CNCCNC>O1CCOCC1.[Cu]I>[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH:12][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[N:25]=[C:26]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:27][C:28]=2[CH3:29])=[CH:22][CH:23]=1)=[O:11]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 691112-ChlorobenzamideHCID 574653764-(4-Bromophenyl)-5-methyl-2-phenyloxazole

Product 1

HCID 445483752-chloro-N-(4-(5-methyl-2-phenyloxazol-4-yl)phenyl)benzamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of potassium carbonate (0.898 g, 6.50 mmol), copper(I) iodide (0.0309 g, 0.162 mmol), 2-chlorobenzamide (0.607 g, 3.90 mmol) and 4-(4-bromophenyl)-5-methyl-2-phenyloxazole (1.021 g, 3.25 mmol) in 10 mL 1,4-dioxane was added N,N′-dimethylethylenediamine (0.0350 ml, 0.325 mmol). The reaction was purged with nitrogen twice (evacuated-backfill) then heated in a 110° C. oil bath. After ca. 72 h the reaction was filtered and the filtrate concentrated under reduced pressure. The concentrate was triturated several times with ethyl acetate and the collected solid was discarded. The product was purified from the filtrate by chromatography on silica gel, eluting with 20-60% ethyl acetate in hexane, to afford product as a faintly yellow solid. ESI+ m/z=389.0 [MH]+.

Workup

  1. customThe reaction was purged with nitrogen twice (evacuated-backfill)
  2. filtrationAfter ca. 72 h the reaction was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe concentrate was triturated several times with ethyl acetate
  5. customThe product was purified from the filtrate by chromatography on silica gel
  6. washeluting with 20-60% ethyl acetate in hexane
  7. customto afford product as a faintly yellow solid

Sources & evidence

ORD record
ord-34436d86eb1740639b80a45f03bf36c1
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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