m-Chloroperbenzoic acid → HCID 59215190, compound

HRID 1171877Notes

Reaction equation

HRID 1171877 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH3:13])[CH2:10][S:11][CH3:12])=[CH:4][N:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:19]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH3:13])[CH2:10][S:11]([CH3:12])=[O:19])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59215205HCID 59215205, compound

Product 1

HCID 59215190HCID 59215190, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-chloro-5-[2-methyl-3-(methylthio)propyl]-pyridine (2.60 g, 12.5 mmol) in CH2Cl2 (35 mL) cooled to −15° C. in an ice-salt bath was added m-chloroperoxybenzoic acid (mCPBA, ˜85%, 2.54 g, ˜12.5 mmol) portion wise at such a rate that the temperature never rose above −10° C. After the addition was over, TLC showed that a single product plus a small amount of starting material was present in the solution. To avoid any sulfone formation, the reaction was quenched at this point by the addition of saturated NaHCO3 (50 mL). The organic layer was separated and the aqueous phase washed with CH2Cl2 (25 mL). The combined organic layers were dried over MgSO4 and the solvent was evaporated to give 2.66 g of crude product as a yellow oil. The oil was triturated with hot hexane (50 mL) and the hexane decanted after cooling. This procedure removed most of the starting material and the resulting product (a mixture of two diastereomers) was directly used for the following step without further purification. [M+H]+=232, 234; δ 1.09 (overlapping d, 3H), 2.57, 2.59 (2 s, 3H).

Workup

  1. additionAfter the addition
  2. customthe reaction was quenched at this point by the addition of saturated NaHCO3 (50 mL)
  3. customThe organic layer was separated
  4. washthe aqueous phase washed with CH2Cl2 (25 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e4f5f4b731214108a97efe46429d20ad
Source dataset
uspto-grants-2010_11
Patent number
US07829719B2

Reaction notes

Loading…