Hydrazine hydrate (1:1) → HCID 86615301, compound

HRID 12904Notes

Reaction equation

HRID 12904 reaction equation
O.[NH2:2][NH2:3].Br[CH2:5][CH2:6][O:7][C:8]([CH3:11])([CH3:10])[CH3:9]>C(O)C>[C:8]([O:7][CH2:6][CH2:5][NH:2][NH2:3])([CH3:11])([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 123592832-(2-Bromoethoxy)-2-methylpropane

Product 1

HCID 86615301HCID 86615301, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of hydrazine monohydrate (36.0 mL, 0.750 mol) in ethanol (70 mL) at 0° C. in an ice-water bath was added 2-(2-bromoethoxy)-2-methylpropane (12.1 mL, 0.075 mol) drop-wise over 20 minutes. The reaction was then allowed to warm to room temperature and stir for 5 minutes and then heated to 40° C. in a preheated oil bath for 4 hours. The reaction was then cooled to room temperature and concentrated to remove the ethanol. To the flask was added water (20 mL) and the aqueous layer was extracted with diethyl ether (2×100 mL). The organic layers were combined and dried over anhydrous Na2SO4, filtered and concentrated to provide (2-tert-butoxyethyl)-hydrazine as a colorless oil (6.05 g, 61%).

Workup

  1. temperatureheated to 40° C. in a preheated oil bath for 4 hours
  2. temperatureThe reaction was then cooled to room temperature
  3. concentrationconcentrated
  4. customto remove the ethanol
  5. additionTo the flask was added water (20 mL)
  6. extractionthe aqueous layer was extracted with diethyl ether (2×100 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3588cffdb1fd4428bec73a63ad14976a
Source dataset
uspto-grants-2010_06
Patent number
US07728029B2

Reaction notes

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