Triethylamine → HCID 59550888, compound

HRID 1169715Notes

Reaction equation

HRID 1169715 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.[C:21](Cl)(=[O:24])[CH2:22][CH3:23]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH3:13])(=[N:12][C:21](=[O:24])[CH2:22][CH3:23])=[O:11])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 12463933S-Methyl-S-(4-nitrophenyl)sulfoximine

Product 1

HCID 59550888HCID 59550888, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

400 mg (2 mmol) (RS)—S-(4-nitrophenyl)-S-methylsulfoximide (Example 1b) are dissolved in 15 ml dichloromethane, cooled in the ice-bath and treated with 0.36 ml triethylamine. 185 mg (2 mmol) propionyl 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)), 489 mg (96%) 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-435a0efdef2d4ee9ab21aa97eb64aa21
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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