Dimethylformamide → HCID 58905142, compound

HRID 272590Notes

Reaction equation

HRID 272590 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 (IC).

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-745e53c926b94179a0e2d3d6296a9bde
Source dataset
uspto-grants-2008_11
Patent number
US07456185B2

Reaction notes

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