Methylamine → Cyclopropanecarboxamide, N,2,2,3,3-pentamethyl-

HRID 1418043Notes

Reaction equation

HRID 1418043 reaction equation
[CH3:1][C:2]1([CH3:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7](Cl)=[O:8].[CH3:11][NH2:12]>C1COCC1>[CH3:11][NH:12][C:7]([CH:3]1[C:2]([CH3:10])([CH3:1])[C:4]1([CH3:6])[CH3:5])=[O:8]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chloride

Product 1

HCID 177237Cyclopropanecarboxamide, N,2,2,3,3-pentamethyl-Yield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,2,3,3-tetramethylcyclopropanecarbonyl chloride (16.05 g, 0.1 mole) in the THF (50 ml) was added slowly to 35% aqueous methyl amine (200 ml). The reaction mixture was stirred for 24 hours at room temperature, and, after removal of THF under reduced pressure, was extracted with CH2Cl2 (2×50 ml). The CH2Cl2 extract was washed successively with H2O (2×100 ml), 0.3 N HCl (200 ml), 0.1 NaHCO3 (100 ml) and saturated NaCl (150 ml), dried over MgSO4 and evaporated to dryness under reduced pressure. The crude product was treated with hexane (100 ml) at room temperature for 30 minutes, filtered and dried to afford 10.5 g (68 mmole, 68%) of a white solid, m.p.: 98° C.

Workup

  1. customafter removal of THF under reduced pressure
  2. extractionwas extracted with CH2Cl2 (2×50 ml)
  3. extractionThe CH2Cl2 extract
  4. washwas washed successively with H2O (2×100 ml), 0.3 N HCl (200 ml), 0.1 NaHCO3 (100 ml) and saturated NaCl (150 ml)
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness under reduced pressure
  7. additionThe crude product was treated with hexane (100 ml) at room temperature for 30 minutes
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-1a73c23d0ad6443884c64a677e663fae
Source dataset
uspto-grants-1999_03
Patent number
US05880157

Reaction notes

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