3-Butyn-2-amine, 2-methyl- → HCID 13131826, compound

HRID 325659Notes

Reaction equation

HRID 325659 reaction equation
[C:1]([C:3]1[CH:14]=[C:13]([NH:15][C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][CH:7]([OH:10])[CH2:8]Cl)#[N:2].[CH3:25][C:26]([NH2:30])([C:28]#[CH:29])[CH3:27]>C(O)C>[C:1]([C:3]1[CH:14]=[C:13]([NH:15][C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:4]=1[O:5][CH2:6][CH:7]([OH:10])[CH2:8][NH:30][C:26]([CH3:27])([C:28]#[CH:29])[CH3:25])#[N:2]

Participants

4

Reactant 2

HCID 763193-Butyn-2-amine, 2-methyl-HCID 20463946HCID 20463946, compound

Product 1

HCID 13131826HCID 13131826, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9 gm of 1-[2-cyano-4-(4-fluorobenzoyl-amino)phenoxy]-3-chloro-propan-2-ol were dissolved in 80 ml of ethanol, and 12.5 ml of 2-methyl-but-3-in-2-amine were added to the solution. After the mixture had been refluxed for 4 hours, the solvent was distilled off in vacuo, the residue was acidified with dilute HCl and washed with ether. The aqueous phase was made alkaline with NH4OH, the base precipitated thereby was extracted twice with ethyl acetate, and the organic phase was washed with H2O and dried over MgSO4. After the ethyl acetate had been distilled off, the crystalline residue was recrystallized twice from acetonitrile. 2.8 gm of colorless crystals of the base were isolated.

Workup

  1. temperatureAfter the mixture had been refluxed for 4 hours
  2. distillationthe solvent was distilled off in vacuo
  3. washwashed with ether
  4. customthe base precipitated
  5. extractionthereby was extracted twice with ethyl acetate
  6. washthe organic phase was washed with H2O
  7. dry with materialdried over MgSO4
  8. distillationAfter the ethyl acetate had been distilled off
  9. customthe crystalline residue was recrystallized twice from acetonitrile

Sources & evidence

ORD record
ord-ea0022b81c5241babafbabbe63754cbb
Source dataset
uspto-grants-1984_04
Patent number
US04442121

Reaction notes

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