3-Butyn-2-amine, 2-methyl- → HCID 13131825, compound

HRID 325658Notes

Reaction equation

HRID 325658 reaction equation
[C:1]([C:3]1[CH:14]=[C:13]([NH:15][C:16]([CH:18]2[CH2:21][CH2:20][CH2:19]2)=[O:17])[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][CH:7]([OH:10])[CH2:8]Cl)#[N:2].[CH3:22][C:23]([NH2:27])([C:25]#[CH:26])[CH3:24]>C(O)C>[C:1]([C:3]1[CH:14]=[C:13]([NH:15][C:16]([CH:18]2[CH2:21][CH2:20][CH2:19]2)=[O:17])[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][CH:7]([OH:10])[CH2:8][NH:27][C:23]([CH3:24])([C:25]#[CH:26])[CH3:22])#[N:2]

Participants

4

Reactant 2

HCID 763193-Butyn-2-amine, 2-methyl-HCID 13136801HCID 13136801, compound

Product 1

HCID 13131825HCID 13131825, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.5 gm (0.024 mol) of 1-(2-cyano-4-cyclobutylcarbonylamino-phenoxy)-2-hydroxy-3-chloro-propane were dissolved in 20 ml of ethanol, 8.3 gm (0.1 mol) of 2-methyl-but-3-in-2-yl-amine were added to the solution, and the mixture was refluxed for 3.5 hours. The ethanol was then distilled off, and the residue was digested with H2O. After being acidified with HCl, the mixture was washed with ether, the acidic aqueous phase was made alkaline with NH4OH, and the base precipitated thereby was extracted by shaking twice with ethyl acetate. The organic phase was washed with H2O, dried over MgSO4 and the ethyl acetate was distilled off in vacuo. The crystalline residue (base) was recrystallized twice from acetonitrile, and 3.7 gm of pure substance were obtained. Melting point: 139°-141° C.

Workup

  1. temperaturethe mixture was refluxed for 3.5 hours
  2. distillationThe ethanol was then distilled off
  3. washthe mixture was washed with ether
  4. customthe base precipitated
  5. extractionthereby was extracted
  6. washThe organic phase was washed with H2O
  7. dry with materialdried over MgSO4
  8. distillationthe ethyl acetate was distilled off in vacuo
  9. customThe crystalline residue (base) was recrystallized twice from acetonitrile, and 3.7 gm of pure substance
  10. customwere obtained

Sources & evidence

ORD record
ord-a751584f4af74c9796c0416687464c44
Source dataset
uspto-grants-1984_04
Patent number
US04442121

Reaction notes

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