(p-Tolylsulphonyl)acetone → 1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-[1-(4-methylphenylsulfonyl)-2-propylidene]hydrazine

HRID 579261

Reaction equation

HRID 579261 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=[O:18])[C:13]([N:15]([CH3:17])[NH2:16])=[O:14])[CH3:2].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH2:29][C:30](=O)[CH3:31])(=[O:28])=[O:27])=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=[O:18])[C:13]([N:15]([CH3:17])[N:16]=[C:30]([CH3:31])[CH2:29][S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:19])=[CH:21][CH:22]=1)(=[O:28])=[O:27])=[O:14])[CH3:2]

Participants

4

Reactant 2

HCID 79327(p-Tolylsulphonyl)acetoneHCID 569428781-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazine

Product 1

HCID 866893571-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-[1-(4-methylphenylsulfonyl)-2-propylidene]hydrazineYield 124.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 25 ml volume three-necked flask with Dean-Stark, 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazine ((12-2)-(11)-39) (500 mg), toluene (1.75 ml), and 1-(4-methylphenylsulfonyl)-2-propanone (7-2-4) (470 mg) were added. Water was removed by azeotropic distillation at 45-50° C. under 100 mmHg for 1.5 hours. To the mixture, toluene (1.75 ml) was added, and water was removed by azeotropic distillation at 60° c. under 120 mmHg for 6 hours. The reaction mixture was concentrated under reduced pressure to give 1.109 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-[1-(4-methylphenylsulfonyl)-2-propylidene]hydrazine ((4-36)-(1)-39).

Workup

  1. customWater was removed by azeotropic distillation at 45-50° C. under 100 mmHg for 1.5 hours
  2. additionTo the mixture, toluene (1.75 ml) was added
  3. customwater was removed by azeotropic distillation at 60° c
  4. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f57beb3b228c4e5e86d2421b894930b5
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Linked notes

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