Hydrochloric Acid → HCID 21707726, compound

HRID 964322Notes

Reaction equation

HRID 964322 reaction equation
[I-].[Li+].[OH:3][CH:4]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]([O:28]C)=[O:27])[CH:19]=1)[CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]1[S:11][CH2:10][CH2:9][CH2:8][S:7]1.Cl>N1C=CC=CC=1>[OH:3][CH:4]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]([OH:28])=[O:27])[CH:19]=1)[CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]1[S:11][CH2:10][CH2:9][CH2:8][S:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 21707727HCID 21707727, compound

Product 1

HCID 21707726HCID 21707726, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of anhydrous lithium iodide (2.68 g, 20 mmol, Aldrich) in 25 mL dry pyridine was brought to reflux under a nitrogen atmosphere and treated with 3 (1.95 g, 5 mmol). The reaction was refluxed for 6 h, then allowed to cool to room temperature under a stream of nitrogen. The solution was poured into 1N HCl (300 mL), and extracted with ethyl acetate (3 X 50 mL). The combined ethyl acetate layers were extracted with 5% sodium bicarbonate (4 X 50 mL). The aqueous phase was acidified to pH 2, and extracted with ethyl acetate (3 X 50 mL). The organic phase was dried with Mg2SO4, filtered through activated charcoal, evaporated, and triturated with hexanes to yield a white solid. Yield: 1.71 g (91%). mp 99°-101° C. IR: 3448 (br), 1735, 1595, 1462, 1232, 719 cm-1. 1H NMR (CDCl3, TMS) d 7.656 (dd, J=8.00, 1.71 Hz, 2 H), 7.299-7.254 (m, 3 H), 7.036 (t, J=7.98 Hz, 1 H), 6.794-6.773 (m, 1 H), 6.573 (d, J=7.55 Hz, 1 H), 6.251 (s, 1 H), 4.955 (s, 1 H), 4.357 (s, 2 H), 2.728-2.620 (m, 4 H), 1.914-1.868 (m, 2 H). 13C NMR (CDCl3, TMS) d 173.47, 156.32, 139.01, 137.40, 130.50, 128.12, 128.07, 127.56, 122.02, 115.43, 113.66, 80.56, 66.13, 64.73, 27.26, 26.96, 24.67. Anal. Calcd. for C19H20O4S2 : C, 60.62; H, 5.35. Found: C, 60.36; H, 5.21.

Workup

  1. temperatureto reflux under a nitrogen atmosphere
  2. temperatureThe reaction was refluxed for 6 h
  3. extractionextracted with ethyl acetate (3 X 50 mL)
  4. extractionThe combined ethyl acetate layers were extracted with 5% sodium bicarbonate (4 X 50 mL)
  5. extractionextracted with ethyl acetate (3 X 50 mL)
  6. dry with materialThe organic phase was dried with Mg2SO4
  7. filtrationfiltered through activated charcoal
  8. customevaporated
  9. customtriturated with hexanes
  10. customto yield a white solid

Sources & evidence

ORD record
ord-58a7279779344736a0cf84a848648ada
Source dataset
uspto-grants-1998_06
Patent number
US05767288

Reaction notes

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