Triethylamine → HCID 21393486, compound

HRID 1606787Notes

Reaction equation

HRID 1606787 reaction equation
Cl.[CH3:2][O:3][NH2:4].C(N(CC)CC)C.[CH:12]1([N:22]=[C:23]=[O:24])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][CH2:13]1>C(Cl)Cl>[CH3:2][O:3][NH:4][C:23]([NH:22][CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][CH2:13]1)=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 162172391-Isocyanato-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 21393486HCID 21393486, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
15 °C

Procedure

To an ice-cold, stirred mixture of 6.7 grams (0.080 mole) of methoxyamine hydrochloride in 80 ml of methylene chloride is added a solution of 8.1 grams (0.080 mole) of triethylamine in 20 ml of methylene chloride. The mixture is stirred at 15°C. for 15 minutes, and is then allowed to warm to 15°C. to 25°C. while a solution of 6.94 grams (0.04 mole) of 1,2,3,4-tetrahydro-1-naphthyl isocyanate in 25 ml of methylene chloride is added dropwise. The mixture is stirred for 30 minutes at room temperature and then filtered. The filtrate is washed with water, dried (sodium sulfate), and the solvent evaporated at reduced pressure to give a solid. Recrystallization of the solid from acetone/hexane gives 6.75 grams of the product, melting point 122°C. to 125°C. Recrystallization of the product from acetone/hexane gives the analytical sample, melting point 123.5°C. to 125°C.

Workup

  1. additionis added dropwise
  2. stirringThe mixture is stirred for 30 minutes at room temperature
  3. filtrationfiltered
  4. washThe filtrate is washed with water
  5. dry with materialdried (sodium sulfate)
  6. customthe solvent evaporated at reduced pressure
  7. customto give a solid
  8. customRecrystallization of the solid from acetone/hexane

Sources & evidence

ORD record
ord-5bd89e8ccb354e7da4b38b1d2f425c0a
Source dataset
uspto-grants-1976_04
Patent number
US03953606

Reaction notes

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