Sodium Thiosulfate → HCID 12112434, compound

HRID 1838093Notes

Reaction equation

HRID 1838093 reaction equation
[F:1][C:2]([F:20])([F:19])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)=[O:13])[OH:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C([O-])(O)=O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(C)(C)C.C(Cl)Cl>[F:20][C:2]([F:1])([F:19])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)=[O:13])=[O:4]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 12112446HCID 12112446, compound

Product 1

HCID 12112434HCID 12112434, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of N-[2-(2,2,2-trifluoro-1-hydroxyethyl)phenyl]furan-2-carboxamide from Step 3 (336 mg, 1.18 mmol) and methylene chloride (31 mL) was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxyl-3(1H)-one (2.00 g, 4.72 mmol), followed by tert-butanol (3.1 mL) under an argon atmosphere at 23° C. After 18 h, sat'd NaHCO3 (31 mL) was added followed by solid sodium thiosulfate (5.20 g, 32.9 mmol). After 1 h at 23° C., the organic layer was separated from the aqueous. The aqueous layer was extracted with ether (2×100 mL), and the combined organics were washed with sat'd NaHCO3:sat'd Na2S2O3 (3×80 mL) and brine (1×80 mL), and dried (MgSO4). After concentration in vacuo, the crude residue was purified by flash chromatography (ethyl acetate:hexane 1:3) which afforded (312 mg) as a yellow gum: 1H NMR (CDCl3) δ6.60 (m), 7.20-7.35 (m), 7.67 (br s), 7.75 (m), 8.03 (m), 9.01 (d, J=6 Hz), 11.93 (brs); 13C NMR (CDCl3) 112.5, 114.6, 115.4, 116.1, 118.4, 121.2, 122.4 (q, J=280 Hz), 122.8, 131.8, 131.9,137.6, 143.1, 145.2, 156.7. MS (EI) 283 (M+), 258, 256, 214. IR (neat) 1674 cm−1. Anal. Calc'd. for C13H8NO3F3: C, 55.13; H, 2.85; N, 4.95. Found: C, 51.01; H, 2.66; N, 4.52.

Workup

  1. waitAfter 1 h at 23° C.
  2. customthe organic layer was separated from the aqueous
  3. extractionThe aqueous layer was extracted with ether (2×100 mL)
  4. washthe combined organics were washed with sat'd NaHCO3
  5. dry with materialsat'd Na2S2O3 (3×80 mL) and brine (1×80 mL), and dried (MgSO4)
  6. concentrationAfter concentration in vacuo
  7. customthe crude residue was purified by flash chromatography (ethyl acetate:hexane 1:3) which
  8. customafforded (312 mg) as a yellow gum

Sources & evidence

ORD record
ord-0c9ea99fd7064d7f85ef75c00c20ab27
Source dataset
uspto-grants-2004_01
Patent number
US06673788B2

Reaction notes

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