Water → HCID 57526993, compound

HRID 1452562Notes

Reaction equation

HRID 1452562 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].C([O-])([O-])=O.[K+].[K+].O.[Cl:13][CH:14]([Cl:18])[C:15](Cl)=[O:16]>C1(C)C=CC=CC=1>[Cl:13][CH:14]([Cl:18])[C:15]([N:3]([O:4][CH3:5])[CH3:2])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6593Dichloroacetyl chlorideHCID 11430Potassium CarbonateHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 57526993HCID 57526993, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

N,O-Dimethylhydroxylamine hydrochloride (7.94 g, 81.4 mmol) and K2CO3 (17.2 g, 124.1 mmol) were added to a water (70 ml) and toluene (70 ml) mixture. The mixture was then cooled to 0° C. Dichloroacetyl chloride (10 g, 67.85 mmol) was added drop wise and the reaction was allowed to warm to room temperature overnight. The toluene was collected and then the aqueous layer was extracted with EtOAc (2×100 ml). The organic layers were dried over sodium sulfate and concentrated in vacuo to give the title product (10.8 g).

Workup

  1. temperatureto warm to room temperature overnight
  2. customThe toluene was collected
  3. extractionthe aqueous layer was extracted with EtOAc (2×100 ml)
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b595e9f5b3624abbb987f3ade259afd8
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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