Water → N-Hydroxy-3-trimethylsilyl-prop-2-ynimidoyl chloride

HRID 2040844Notes

Reaction equation

HRID 2040844 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[C:3]#[C:4][CH:5]=[N:6][OH:7].[Cl:10]N1C(=O)CCC1=O.O>CN(C=O)C>[OH:7][N:6]=[C:5]([Cl:10])[C:4]#[C:3][Si:2]([CH3:9])([CH3:8])[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 731658473-Trimethylsilylprop-2-ynal oxime

Product 1

HCID 86662874N-Hydroxy-3-trimethylsilyl-prop-2-ynimidoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-trimethylsilylprop-2-ynal oxime (Carreira, Erick M.; Lohse-Fraefel, Nina, Organic Letters, Volume 7, Issue 10, 2005, Pages 2011-20141, 68 g, 11.9 mmol) in 11.9 mL of DMF stirred at r.t. was added N-chlorosuccinimide (1.99 g, 14.8 mmol). After 4 h stirring, the solution was poured into water and extracted with Et2O. After the usual work-up, the residue (2.09 g) was used as it was for the next step.

Workup

  1. extractionextracted with Et2O

Sources & evidence

ORD record
ord-ce61971d78644b359320d199c61a3595
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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