Triethylamine → HCID 68601237, compound

HRID 1799674Notes

Reaction equation

HRID 1799674 reaction equation
O[CH2:2][C:3]1[N:4]=[CH:5][S:6][C:7]=1/[CH:8]=[CH:9]\[S:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.S(Cl)([Cl:39])=O.O.C(=O)(O)[O-].[Na+]>C1COCC1.[Cl-].[Na+].O>[Cl:39][CH2:2][C:3]1[N:4]=[CH:5][S:6][C:7]=1/[CH:8]=[CH:9]\[S:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 68599758HCID 68599758, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 68601237HCID 68601237, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 816 mg of 4-hydroxymethyl-5-((Z)-2-tritylthioethen-1-yl)thiazole prepared in step e) in Example 1 in 25 ml of THF was cooled in ice, and 0.301 ml of triethylamine and 0.157 ml of thionyl chloride were added to the cooled solution under an argon atmosphere. The mixture was stirred at the same temperature for 20 min, brine was then added to the reaction solution, and the mixture was adjusted to pH 8 by the addition of sodium bicarbonate water. The mixture was extracted twice with ethyl acetate. The organic layers were combined, were washed with brine, were 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 to 1:1) to give 512 mg of 4-chloromethyl-5-((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 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 to 1:1)

Sources & evidence

ORD record
ord-cbd6f10f6a204169835c635fecdd8977
Source dataset
uspto-grants-2013_01
Patent number
US08344154B2

Reaction notes

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