Tetrahydrofuran → 1-methyl-1-[2-(1-methyl-1H-indol-3-yl)-2-oxoacetyl]-2-(1-methylsulfonyl-2-propylidene)hydrazine

HRID 579254Notes

Reaction equation

HRID 579254 reaction equation
[CH3:1][NH:2][N:3]=[C:4]([CH3:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7].O1CCCC1.[CH3:16][N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26](=[O:30])[C:27](Cl)=[O:28])=[CH:18]1>O>[CH3:1][N:2]([C:27](=[O:28])[C:26]([C:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:17]([CH3:16])[CH:18]=1)=[O:30])[N:3]=[C:4]([CH3:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10799027(1-methyl-1H-indol-3-yl)-oxo-acetyl chlorideHCID 764689591-Methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine

Product 1

HCID 866893561-methyl-1-[2-(1-methyl-1H-indol-3-yl)-2-oxoacetyl]-2-(1-methylsulfonyl-2-propylidene)hydrazineYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 50 ml volume three-necked flask, 1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine (5-2-1) (2.22 g) and tetrahydrofuran (anhydrous) (10 ml) were added under a nitrogen atmosphere. To the mixture, 2-(1-methyl-1H-indol-3-yl)-2-oxoacetyl chloride (26-a) (3.0 g) was added dropwise under ice-cooling, and stirred for 2 hours. The reaction mixture was added to iced water, and the precipitated solids were collected by filtration, washed with water and hexane, and dried under reduced pressure to give 3.4 g of 1-methyl-1-[2(1-methyl-1H-indol-3-yl)-2-oxoacetyl]-2-(1-methylsulfonyl-2-propylidene)hydrazine ((4-203-(13)28).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated solids were collected by filtration
  3. washwashed with water and hexane
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-07467d8d6de84039bd30d49b4ecd02cf
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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