Hydrochloric Acid → HCID 22272570, compound

HRID 2251341Notes

Reaction equation

HRID 2251341 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[H-].[Na+].F[C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17].Cl.N#N>CN(C=O)C.[Cl-].[Na+].O>[F:15][C:13]1[CH:12]=[CH:11][C:10]([N+:16]([O-:18])=[O:17])=[C:9]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 24758Sodium hydrideHCID 679672,4-DifluoronitrobenzeneHCID 72879Methanesulfonamide

Product 1

HCID 22272570HCID 22272570, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Methylsulfonamide (2.421 g, 25.4 mmol) was dissolved in DMF (100 mL) and NaH (60% in oil, 1.00 g, 25 mmol) was added. The reaction stirred for 1 h and added to a stirred solution of 2,4-difluoronitrobenzene (4.372 g, 27.5 mmol) in DMF (20 mL). The reaction mixture was stirred for 2 h, poured into a mixture (1:1) of brine and 1M HCl, and extracted with toluene. The organic phase was dried (MgSO4), and concentrated to give a solid that was crystallized from toluene/petroleum ether. The flask tipped over and some material was lost, to give 1.32 g, 5.64 mmol in 22% yield. MS (posES-FIA) m/z=found: 234; Calcd: 234.01; Anal (C7 H7 F N2 O4 S), C, H, N, S.

Workup

  1. stirringThe reaction mixture was stirred for 2 h
  2. extractionextracted with toluene
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customto give a solid
  6. customthat was crystallized from toluene/petroleum ether
  7. customto give 1.32 g, 5.64 mmol in 22% yield

Sources & evidence

ORD record
ord-cc4f65365edc4d1fa32c4ae35a6ec739
Source dataset
uspto-grants-2008_01
Patent number
US07319097B2

Reaction notes

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