Dichloromethane → 2-cyano-N-(1,1-dimethylethyl)-2-(hydroxyimino)acetamide

HRID 269395Notes

Reaction equation

HRID 269395 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2].[N:11](Cl)=[O:12].C(Cl)Cl>C(Cl)(Cl)Cl>[C:1]([C:3](=[N:11][OH:12])[C:4]([NH:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 17601Nitrosyl chlorideHCID 1515876N-tert-butyl-2-cyanoacetamide

Product 1

HCID 729739832-cyano-N-(1,1-dimethylethyl)-2-(hydroxyimino)acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Cyano-N-(1,1-dimethylethyl)acetamide 11 (Bhawal, B. M.; Khanapure, S. P.; Biehl, E. R.; Syn. Commun., 1990, 20, 3235) is allowed to react with nitrosyl chloride in an inert organic solvent such as CH2Cl2 or CHCl3 at moderate temperature (e.g., ambient temperature to −25° C., preferably about 0° C.). The resulting 2-cyano-N-(1,1-dimethylethyl)-2-(hydroxyimino)acetamide 13 is isolated and reduced, for example with sodium dithionite in an aqueous organic solvent, but preferably with aluminum amalgam in water at moderate temperature (e.g., ambient temperature to about 0° C., preferably about 0° C.).

Sources & evidence

ORD record
ord-e85519abc36241d9a5186d437327a3cb
Source dataset
uspto-grants-2008_11
Patent number
US07446209B2

Reaction notes

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