Triethylamine → HCID 68547563, compound

HRID 2243507Notes

Reaction equation

HRID 2243507 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6](OS(C(F)(F)F)(=O)=O)=[C:7]([C:9]([O:11][CH3:12])=[O:10])[S:8][C:4]=2[CH:3]=1.[CH2:23]([N:25](CC)CC)[CH3:24].C(OC)(=O)C[SH:32]>ClCCl.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6]([S:32][CH2:24][C:23]#[N:25])=[C:7]([C:9]([O:11][CH3:12])=[O:10])[S:8][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 86605575HCID 86605575, compound

Product 1

HCID 68547563HCID 68547563, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 6-chloro-3-{ [(trifluoromethyl)sulfonyl]oxy}-1-benzothiophene-2-carboxylate (2.0 g, 5.3 mmol) and triethylamine (890 μL, 1.2 eq), in dichloromethane (45 mL) was cooled to −20° C. and methyl thioglycolate(908 μL, 2.5 eq) was added dropwise via syringe pump over 5 h. The reaction was allowed to warm to room temperature overnight. The solution was diluted with water, and ethyl acetate, washed with water and brine, dried, filtered, evaporated, and flash chromatographed (10-20% ethyl acetate/hexanes) to provide methyl 6-chloro-3-[(cyanomethyl)thio]-1-benzothiophene-2-carboxylate (1.01 g, 64%) as a white solid.

Workup

  1. washwashed with water and brine
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customflash chromatographed (10-20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-31170ea969a44028a539da79b7a82f79
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

Loading…