Dichloromethane → Acetamide, 2-(diethylamino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)-
Reaction equation
CC[CH2:3][C:4]1[S:8][C:7]([NH:9]C(CN(C)C)=O)=[N:6][N:5]=1.F[C:17](F)(F)[C:18]([NH2:20])=O.[C:23](OI(C1C=CC=CC=1)OC(=O)C)(=O)[CH3:24].[C:38]([O-:41])([O-])=O.[K+].[K+].[CH2:44](Cl)Cl>>[CH3:17][CH2:18][N:20]([CH2:44][C:38]([NH:9][C:7]1[S:8][C:4]([CH3:3])=[N:5][N:6]=1)=[O:41])[CH2:23][CH3:24]Participants
6
Procedure
A mixture of AK-3 (1.0 g, 3.7 mmol), MgO (600 mg, 14.9 mmol), trifluoroacetamide (839 mg, 7.4 mmol), and Rh(II) acetate dimer (115 mg, 0.26 mmol) in DCM (10 mL) is added (diacetoxyiodo)benzene (1.79 g, 5.6 mmol). The mixture is stirred at rt for 18 h and then concentrated under reduced pressure. The resultant residue is dissolved in MeOH, filtered through a pad of diatomaceous earth and to it, K2CO3 (2.55 g, 18.6 mmol) is added. The mixture is stirred at rt for 18 h and is concentrated under reduced pressure. The resultant residue is purified by SiO2 flash chromatography to yield AK-4.
Workup
- concentrationconcentrated under reduced pressure
- dissolutionThe resultant residue is dissolved in MeOH
- additionis added
- stirringThe mixture is stirred at rt for 18 h
- concentrationis concentrated under reduced pressure
- customThe resultant residue is purified by SiO2 flash chromatography
Sources & evidence
- ORD record
- ord-692e62c09d2e45bdaba1ddab76899a11
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242989B2
Reaction notes
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