Triethylamine → (RS)-S-(4-nitrophenyl)-N-(2-methoxy-acetyl)-S-methylsulfoximide

HRID 38210Notes

Reaction equation

HRID 38210 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[NH:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH3:21][O:22][CH2:23][C:24](Cl)=[O:25]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH3:13])(=[N:12][C:24](=[O:25])[CH2:23][O:22][CH3:21])=[O:11])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 12463933S-Methyl-S-(4-nitrophenyl)sulfoximine

Product 1

HCID 59550858(RS)-S-(4-nitrophenyl)-N-(2-methoxy-acetyl)-S-methylsulfoximideYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg (0.5 mmol) (RS)—S-(4-nitrophenyl)-S-methylsulfoximide (Example 1b) are dissolved in 3.33 ml dichloromethane, cooled in the ice-bath and treated with 0.1 ml (0.75 mmol) triethylamine. 0.068 ml (0.75 mmol) 2-methoxy-acetyl chloride are added dropwise with ice cooling. The mixture is stirred for 30 minutes in the ice-bath and for 15 hours at room temperature. After chromatographic purification (silica gel, hexane/ethyl acetate (0-50% ethyl acetate)), 107 mg (79%) of the desired product is obtained.

Workup

  1. customAfter chromatographic purification (silica gel, hexane/ethyl acetate (0-50% ethyl acetate))

Sources & evidence

ORD record
ord-11be12865de0467796276e23eb8558b3
Source dataset
uspto-grants-2013_09
Patent number
US08524724B2

Reaction notes

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