Water → HCID 20201569, compound

HRID 979179Notes

Reaction equation

HRID 979179 reaction equation
[CH3:1][NH:2][NH2:3].[C:4](=[O:7])([O-])[O-:5].[K+].[K+].BrCC(O[C:15]([CH3:18])([CH3:17])[CH3:16])=O.O.[CH3:20]N(C)C=O>>[C:15]([CH:1]([C:4]([OH:5])=[O:7])[NH:2][NH:3][CH3:20])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 5

HCID 962WaterHCID 6061MethylhydrazineHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 20201569HCID 20201569, compound

Procedure

To a stirred suspension containing 58.1 mmol of methylhydrazine and 8.04 gm (58.2 mmol) of potassium carbonate in 60 ml of N,N-dimethylformamide at 0° C. is added dropwise over 1 hour 9.59 ml (59.4 mmol) of t-butyl bromoacetate. After stirring for 1 hour at room temperature the reaction mixture is poured into 500 ml of water and extracted three times with ethyl acetate. The combined organic portions are dried over magnesium sulfate, filtered, and concentrated in vacuo. The product is chromatographed to afford N-(t-butylcarboxymethyl)-N'-methyl-hydrazine, which is reacted with an equimolar amount of 4-chloro-3-sulfamoylbenzoyl chloride to yield 1-t-butylcarboxymethyl-2-methyl-2-(4-chloro-3-sulfamoylbenzoyl)hydrazine (VII-B).

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined organic portions are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product is chromatographed

Sources & evidence

ORD record
ord-f3697abe484045e397fa9418b5897964
Source dataset
uspto-grants-1987_05
Patent number
US04666906

Reaction notes

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