Carbon Disulfide → HCID 22139424, compound

HRID 1825805Notes

Reaction equation

HRID 1825805 reaction equation
[C:1](=[S:3])=[S:2].[C:4]1([C:18](=[O:20])[CH3:19])[C:17]2[S:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[S:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.CC(C)([O-])C.[K+]>O1CCCC1>[O:20]=[C:18]([C:4]1[C:17]2[S:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[S:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH2:19][C:1]([SH:3])=[S:2]

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 16203464HCID 16203464, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22139424HCID 22139424, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of CS2 (1.55 ml, 25.5 mmol) and 1-thianthren-1-yl-ethanone (6.59 g, 25.5 mmol) in dry tetrahydrofuran (20 ml) was added drop wise to a solution of potassium t-butoxide (5.73 g, 51 mmol) in dry tetrahydrofuran (50 ml) under N2 at 0° C. A red coloration and the formation of a precipitate were observed. The mixture was left under vigorous stirring over the weekend and was then poured onto water (200 ml) and extracted with ether (3×100 ml). The aqueous was acidified with 2N H2SO4 to pH 1 (Whatmann pH paper) and the extracted with ether (3×100 ml). The organic were dried over magnesium sulphate and the solvent was evaporated in vacuo to give the desired product as a dark orange resin (5.00 g, 59%). m/z (LC-MS, ESP), RT=5.11; (M−−1)=333

Workup

  1. waitThe mixture was left
  2. additionwas then poured onto water (200 ml)
  3. extractionextracted with ether (3×100 ml)
  4. extractionthe extracted with ether (3×100 ml)
  5. dry with materialThe organic were dried over magnesium sulphate
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-94d39481259b47e89835e3d575bae2f1
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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