Triethylamine → HCID 10012348, compound

HRID 1767274Notes

Reaction equation

HRID 1767274 reaction equation
[CH3:1][C:2]1([CH3:10])[CH:4]([C:5](Cl)=[O:6])[C:3]1([CH3:9])[CH3:8].Cl.[O:12]([NH2:14])[CH3:13].C(N(CC)CC)C>ClCCl>[CH3:13][O:12][NH:14][C:5]([CH:4]1[C:2]([CH3:10])([CH3:1])[C:3]1([CH3:9])[CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chloride

Product 1

HCID 10012348HCID 10012348, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Tetramethylcyclopropanecarbonyl chloride (TMC-Cl) (4 g; 25 mmol) dissolved in 20 ml of dry dichloromethane was slowly added to a stirred and dry dichloromethane solution of methoxylamine hydrochloride (2.5 g; 30 mmol) and triethylamine (6.3 g; 50 mmol). After the addition, the reaction mixture was stirred for 2 hr at room temperature. Dichloromethane was evaporated under vacuum, 10 ml of water was added and the products were extracted using 30 ml of ethyl acetate. The organic fraction was dried over MgSO4, filtered and evaporated under vacuum. The product was crystallized using 20 ml ethyl acetate and 30 ml petroleum ether to afford 3 g (75% yield) and its chemical structure was identified by elemental analysis and spectroscopic methods.

Workup

  1. additionwas slowly added to
  2. additionAfter the addition
  3. stirringthe reaction mixture was stirred for 2 hr at room temperature
  4. customDichloromethane was evaporated under vacuum, 10 ml of water
  5. additionwas added
  6. extractionthe products were extracted
  7. dry with materialThe organic fraction was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated under vacuum
  10. customThe product was crystallized
  11. customto afford 3 g (75% yield) and its chemical structure

Sources & evidence

ORD record
ord-112bfaf24afb4065964848a4ef512747
Source dataset
uspto-grants-2007_06
Patent number
US07232929B2

Reaction notes

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