Acetic Acid → Acetamide, 2-(dimethylamino)-N-(5-propyl-1,3,4-thiadiazol-2-yl)-

HRID 594921Notes

Reaction equation

HRID 594921 reaction equation
[CH3:1][CH2:2][C:3]1[S:7][C:6]([NH:8][C:9]([CH2:11][N:12]([CH3:14])[CH3:13])=[O:10])=[N:5][N:4]=1.OO.[CH3:17]C(O)=O>>[CH3:17][CH2:1][CH2:2][C:3]1[S:7][C:6]([NH:8][C:9]([CH2:11][N:12]([CH3:14])[CH3:13])=[O:10])=[N:5][N:4]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 1091545Acetamide, 2-(dimethylamino)-N-(5-ethyl-1,3,4-thiadiazol-2-yl)-

Product 1

HCID 3076716Acetamide, 2-(dimethylamino)-N-(5-propyl-1,3,4-thiadiazol-2-yl)-

Procedure

To solution of AK-2 (3.3 g, 13.1 mmol) in AcOH (10 mL) is slowly added H2O2 (1.37 mL, 13.7 mmol). The reaction mixture is stirred at rt for 3 h and is then quenched with saturated Na2SO3(aq) and neutralized with 1N NaOH(aq). The mixture is extracted with EtOAc and concentrated to yield AK-3.

Workup

  1. customis then quenched with saturated Na2SO3(aq)
  2. extractionThe mixture is extracted with EtOAc
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b94aa5acf07c4bd4a85c5bb12cfcb8cc
Source dataset
uspto-grants-2016_01
Patent number
US09242989B2

Reaction notes

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