Dimethylformamide → HCID 136332415, compound

HRID 2400270Notes

Reaction equation

HRID 2400270 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:8]=[C:7](I)[C:3]=1[C:4]([OH:6])=O.Cl.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH2:25])=O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C[N:35](C)C=O>C(OCC)(=O)C.[Cu]I>[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]2[NH:35][C:4](=[O:6])[C:3]3[C:7](=[CH:8][C:9]([C:12]([F:15])([F:14])[F:13])=[C:10]([F:11])[C:2]=3[F:1])[N:25]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 18176656HCID 18176656, compoundHCID 86667786HCID 86667786, compound

Product 1

HCID 136332415HCID 136332415, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of crude 2,3-difluoro-6-iodo-4-trifluoromethylbenzoic acid (1.00 g), 4-chlorobenzamide hydrochloride (0.814 g, 4.26 mmol), copper (I) iodide (0.108 g), caesium carbonate (1.85 g, 5.68 mmol) in dimethylformamide (8 mL) were stirred under nitrogen at room temperature for 1 week. The reaction mixture was then diluted with ethyl acetate (100 mL) and washed with hydrochloric acid (1 M, 25 mL) and water (25 mL). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure (0.98 g). The reaction was repeated with crude 2,3-difluoro-6-iodo-4-trifluoromethylbenzoic acid (0.50 g) to afford an additional portion (0.57 g) of the quinazolin-4-one. LC-MS: 3.6 min, 361 (M+).

Workup

  1. washwashed with hydrochloric acid (1 M, 25 mL) and water (25 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure (0.98 g)

Sources & evidence

ORD record
ord-468f6db9dfc54339b4156890ea5d9d40
Source dataset
uspto-grants-2014_08
Patent number
US08796180B2

Reaction notes

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