Hydrochloric Acid → 2-fluoro-4-formyl-N-(2-hydroxy-5-(phenylthio)phenyl)benzamide

HRID 2075264Notes

Reaction equation

HRID 2075264 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C(Cl)=O.Cl.[NH2:20][C:21]1[CH:26]=[C:25]([S:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:23][C:22]=1[OH:34].C(N(C(C)C)CC)(C)C.Cl>C(Cl)Cl.CN(C=O)C.C1COCC1>[F:1][C:2]1[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH:20][C:21]1[CH:26]=[C:25]([S:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:23][C:22]=1[OH:34])=[O:6]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 184419582-Fluoro-4-formylbenzoic acidHCID 670921602-Amino-4-(phenylthio)phenol hydrochloride

Product 1

HCID 584152542-fluoro-4-formyl-N-(2-hydroxy-5-(phenylthio)phenyl)benzamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of 2-fluoro-4-formylbenzoic acid (0.600 g, 3.57 mmol) in 10 mL anhydrous DCM under nitrogen was added 3 drops DMF, followed by oxalyl chloride (0.380 mL, 4.28 mmol). The reaction was allowed to stir under N2. The reaction was allowed to stir for 4 h and concentrated in vacuo to a yellow oil. This material was dissolved in 10 mL THF and was added via pipette to a slurry of 2-amino-4-(phenylthio)phenol hydrochloride (0.906 g, 3.57 mmol) and diisopropylethylamine (1.55 mL, 8.92 mmol) in THF at 0° C. The bright yellow slurry was allowed to stir overnight. The mixture was treated with 1N HCl and DCM, and the organic layer was extracted 1×DCM. The organics were dried, filtered, and concentrated in vacuo. The orange oil was dissolved in 5 mL DCM, and a thick yellow precipitate resulted. This was collected by filtration, rinsing with DCM to give 2-fluoro-4-formyl-N-(2-hydroxy-5-(phenylthio)phenyl)benzamide as a bright yellow solid. MS (ESI) m/z: Calculated: 367.1; Observed: 366.0 (M−−1).

Workup

  1. stirringto stir for 4 h
  2. concentrationconcentrated in vacuo to a yellow oil
  3. dissolutionThis material was dissolved in 10 mL THF
  4. stirringto stir overnight
  5. extractionthe organic layer was extracted 1×DCM
  6. customThe organics were dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe orange oil was dissolved in 5 mL DCM
  10. customa thick yellow precipitate resulted
  11. filtrationThis was collected by filtration
  12. washrinsing with DCM

Sources & evidence

ORD record
ord-85ad3c7885514275b1d640a9dbb77b63
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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