HCID 86745490, compound → HCID 86745489, compound

HRID 1534623Notes

Reaction equation

HRID 1534623 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][C:15](=[O:18])[S:16][CH:17]=2)=[CH:9][CH:8]=1)(=O)C>CO.O>[O:18]=[C:15]1[S:14][C:13]([C:10]2[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][OH:4])=[CH:12][CH:11]=2)=[CH:17][S:16]1

Participants

4

Reactant 1

HCID 86745490HCID 86745490, compound

Product 1

HCID 86745489HCID 86745489, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of compound 7 (40.0 g, 0.143 mol) dissolved in 500 ml methanol and 40 g K2C03 dissolved in 300 ml water was stirred at room temperature for 1 hour. The mixture was extracted with 300 ml chloroform. The chloroform solution was washed with water, concentrated, recrystallized (methanol/ether), and dried to give 23.8 g (70.0%) of compound 8. Analysis of the product gave the following results: mp 92°-94° C.; NIR (KBr) 3258, 3060, 2927, 1697, 1632, 1503, 1055, 1046, 868 cm-1 ; 1H NMR (300 MHz) δ 1.55 (s, 1H), 2.89 (t, 2H, J=6.8 Hz), 3.88 (t, 2H, J=6.8 Hz), 6.79 (s, 1H), 7.26-7.38 (m, 4H); 13C NMR (75 MHz) δ 192.52, 140.08, 134.80, 130.89, 129.79, 126.43, 111.19, 63.27, 38.75. Anal. Calcd. for C 11 H10O2S2 : C, 55.44; H, 4.23; Found: C, 56.32; H, 4.56.

Workup

  1. extractionThe mixture was extracted with 300 ml chloroform
  2. washThe chloroform solution was washed with water
  3. concentrationconcentrated
  4. customrecrystallized (methanol/ether)
  5. customdried

Sources & evidence

ORD record
ord-a95033622f1c4278b795ca8803ac793b
Source dataset
uspto-grants-1992_02
Patent number
US05089585

Reaction notes

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