Tert-Butylamine → HCID 13136802, compound

HRID 325657Notes

Reaction equation

HRID 325657 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].[C:22]([NH2:26])([CH3:25])([CH3:24])[CH3:23]>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:26][C:22]([CH3:25])([CH3:24])[CH3:23])#[N:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 13136801HCID 13136801, compound

Product 1

HCID 13136802HCID 13136802, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.5 gm (0.024 mol) of 1-(2-cyano-4-cyclobutylcarbonylamino-phenoxy)-3-chloro-propan-2-ol were dissolved in 80 ml of ethanol, and the solution was mixed with 8.7 gm (0.12 mol) of tert. butylamine, and the mixture was refluxed for four hours. The solvent was distilled off in vacuo, the residue was extracted by shaking with dilute hydrochloric acid with the addition of ether, and the organic phase was separated. The aqueous phase was washed with ether and made alkaline with NH4OH. The base which precipitated was extracted with ethyl acetate, and the organic phase was dried over MgSO4. The ethyl acetate was distilled off, and the crystalline residue was recrystallized twice from acetonitrile.

Workup

  1. temperaturethe mixture was refluxed for four hours
  2. distillationThe solvent was distilled off in vacuo
  3. extractionthe residue was extracted
  4. customthe organic phase was separated
  5. washThe aqueous phase was washed with ether
  6. customThe base which precipitated
  7. extractionwas extracted with ethyl acetate
  8. dry with materialthe organic phase was dried over MgSO4
  9. distillationThe ethyl acetate was distilled off
  10. customthe crystalline residue was recrystallized twice from acetonitrile

Sources & evidence

ORD record
ord-84f3971879654b8f81e2b6a2f069b091
Source dataset
uspto-grants-1984_04
Patent number
US04442120

Reaction notes

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