Benzenemethanethiol, alpha,alpha-diphenyl- → HCID 68599758, compound

HRID 1799673Notes

Reaction equation

HRID 1799673 reaction equation
[C:1]([C:3]1[S:7][CH:6]=[N:5][C:4]=1[CH2:8][OH:9])#[CH:2].[C:10]1([C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[SH:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CC(C)([O-])C.[K+]>C1COCC1.[Cl-].[Na+].O>[OH:9][CH2:8][C:4]1[N:5]=[CH:6][S:7][C:3]=1/[CH:1]=[CH:2]\[S:17][C:16]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 23665647Potassium tert-butoxideHCID 45121755HCID 45121755, compound

Product 1

HCID 68599758HCID 68599758, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 2.73 g of 5-ethynyl-4-hydroxymethylthiazole in 65 ml of THF was cooled in ice under an argon atmosphere, and 6.5 g of triphenylmethane thiol and 440 mg of potassium-t-butoxide were added to the cooled solution. The mixture was stirred at room temperature for 2 hr. Brine was added to the reaction solution, and the mixture was extracted twice with ethyl acetate. The organic layers were combined, were washed with brine, were then dried over anhydrous magnesium sulfate, were filtered, and were concentrated under the reduced pressure. Ethyl acetate (10 ml) and 10 ml of hexane were added to the residue, and the resultant precipitate was collected by filtration to give 7.26 of the title compound.

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washwere washed with brine
  3. dry with materialwere then dried over anhydrous magnesium sulfate
  4. filtrationwere filtered
  5. concentrationwere concentrated under the reduced pressure
  6. additionEthyl acetate (10 ml) and 10 ml of hexane were added to the residue
  7. filtrationthe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-357c0af59ae445228ede345e72dc3264
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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