Dimethylformamide → HCID 58905142, compound

HRID 1292858Notes

Reaction equation

HRID 1292858 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10](O)=[O:11].S(Cl)(Cl)=O.C[N:27](C=O)C>>[F:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([NH2:27])=[O:11]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 16785176HCID 16785176, compound

Product 1

HCID 58905142HCID 58905142, compound

Procedure

A mixture of compound (1B) (53 g, 0.18 mol), thionyl chloride (51.3 mL) and DMF (1 mL) was stirred at room temperature for 18 h, then concentrated in vacuo to dryness. This acid chloride (60.7 g) was dissolved in THF (400 mL), and NH4OH (235 mL) was added. The mixture was then stirred for 18 h and concentrated in vacuo. The residue was purified by flash chromatography eluting with hexane:EtOAc (4:1) to afford 27.7 g of 5-(2,4-difluoro-phenoxy)-2-nitro-benzamide (1C).

Workup

  1. concentrationconcentrated in vacuo to dryness
  2. dissolutionThis acid chloride (60.7 g) was dissolved in THF (400 mL)
  3. additionNH4OH (235 mL) was added
  4. stirringThe mixture was then stirred for 18 h
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography
  7. washeluting with hexane:EtOAc (4:1)

Sources & evidence

ORD record
ord-68312778239d4fffaf42c44757984b70
Source dataset
uspto-grants-2007_07
Patent number
US07238698B2

Reaction notes

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