Ammonium Chloride → 4-methoxycarbonyl-2-((Z)-2-tritylthioethen-1-yl)thiazole

HRID 1799679Notes

Reaction equation

HRID 1799679 reaction equation
[C:1]([C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:7]=1)#[CH:2].[C:12]1([C:18]([SH:31])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CC(C)([O-])C.[K+].[Cl-].[NH4+]>C1COCC1>[CH3:11][O:10][C:8]([C:6]1[N:7]=[C:3](/[CH:1]=[CH:2]\[S:31][C:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[S:4][CH:5]=1)=[O:9]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 77281Benzenemethanethiol, alpha,alpha-diphenyl-HCID 23665647Potassium tert-butoxideHCID 866098112-Ethynyl-4-methoxycarbonylthiazole

Product 1

HCID 686011224-methoxycarbonyl-2-((Z)-2-tritylthioethen-1-yl)thiazoleYield 58.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Ethynyl-4-methoxycarbonylthiazole (2.50 g) was dissolved in 70 ml of THF. Triphenylmethylmercaptan (4.96 g) and 336 mg of potassium-t-butoxide were added to the solution at −60° C. under an argon atmosphere. The mixture was stirred at the same temperature for one hr. An aqueous ammonium chloride solution 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. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1). Ethyl acetate and hexane were added to a crude product containing a target compound, and the precipitate was collected by filtration to give 3.88 g of 4-methoxycarbonyl-2-((Z)-2-tritylthioethen-1-yl)thiazole.

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. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:1)
  7. additionEthyl acetate and hexane were added to a crude product
  8. additioncontaining a target compound
  9. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c7a663b519d343149c65b7ebaf0aadc0
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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