Carbon Tetrachloride → HCID 20339314, compound

HRID 1395416Notes

Reaction equation

HRID 1395416 reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)(Cl)Cl.[CH3:19][O:20][P:21]([O-:24])[O:22][CH3:23]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.ClCCl>[C:2]([NH:6][NH:7][P:21]([O:22][CH3:23])([O:20][CH3:19])=[O:24])([CH3:5])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 5943Carbon TetrachlorideHCID 11430Potassium CarbonateHCID 81889tert-Butylhydrazine monohydrochlorideHCID 21884954Dimethylphosphite

Product 1

HCID 20339314HCID 20339314, compoundYield 73.9%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of t-butylhydrazine hydrochloride (12.46 g, 0.1 mole), potassium carbonate (27.64 g, 0.2 mole) and triethylbenzyl ammonium chloride (0.3 g, 0.0013 mole) was stirred vigorously at reflux with dichloromethane (100 ml) and carbon tetrachloride (60 ml) for 30 minutes. A solution of dimethylphosphite (11.0 g, 0.1 mole) in dichloromethane (20 ml) was then added dropwise to this refluxing mixture and the mixture stirred and refluxed for an additional 20 hours. The mixture was then filtered and the filtrate dried over anhydrous magnesium sulfate. The dried filtrate, then was evaporated down to a viscous oil which was subjected to high vacuum for 2 or 3 hours to yield 14.5 g of a solid product, m.pt. 61°-8° C.

Workup

  1. stirringthe mixture stirred
  2. temperaturerefluxed for an additional 20 hours
  3. filtrationThe mixture was then filtered
  4. dry with materialthe filtrate dried over anhydrous magnesium sulfate
  5. customThe dried filtrate, then was evaporated down to a viscous oil which
  6. customwas subjected to high vacuum for 2 or 3 hours

Sources & evidence

ORD record
ord-6f4b06c9584746699cf3d8d8aa833518
Source dataset
uspto-grants-1980_05
Patent number
US04203979

Reaction notes

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