Triethylamine → HCID 15163511, compound

HRID 638230Notes

Reaction equation

HRID 638230 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]1([F:35])[O:34][C:16]2=[CH:17][C:18]3[NH:22][C:21]([S:23][CH2:24][C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][N:26]=4)=[N:20][C:19]=3[CH:33]=[C:15]2[O:14]1.C(N(CC)CC)C.C(=O)(O)[O-].[K+]>C(Cl)Cl>[F:35][C:13]1([F:12])[O:34][C:16]2=[CH:17][C:18]3[NH:22][C:21]([S:23]([CH2:24][C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][N:26]=4)=[O:6])=[N:20][C:19]=3[CH:33]=[C:15]2[O:14]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 516893Potassium BicarbonateHCID 15163508HCID 15163508, compound

Product 1

HCID 15163511HCID 15163511, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.91 g of approximately 85% pure m-chloroperoxybenzoic acid in 20 ml of methylene chloride is added dropwise to a solution of 1.5 g of 2,2-difluoro-6-[(4-methoxy-2-pyridyl)methylthio]-5H-[1,3]-dioxolo[4,5-f]benzimidazole in 50 ml of methylene chloride at -30° C. in the course of 5 min., with stirring, and the temperature is allowed to rise to -10° C. in the course of 30 min. 0.62 ml of triethylamine is added, followed by 20 ml of aqueous potassium bicarbonate solution, the title compound already crystallizing out in the cold. The mixture is filtered and the precipitate is washed with water to yield 1.2 g of the title compound. The organic phase is separated off from the filtrate, washed with water and dried with magnesium sulfate and the solution is concentrated completely, at 30° C. A further 0.25 g of the title compound is obtained from the residue by recrystallization from ethyl acetate; total yield: 92%, m.p.: 184°-185° C. (decompositon).

Workup

  1. customto rise to -10° C. in the course of 30 min
  2. customthe title compound already crystallizing out in the cold
  3. filtrationThe mixture is filtered
  4. washthe precipitate is washed with water

Sources & evidence

ORD record
ord-e8953536aea648c9a4debfea41a65c01
Source dataset
uspto-grants-1985_12
Patent number
US04560693

Reaction notes

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