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Triethylamine → HCID 178449016, compound

HRID 1441689
Notes
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Reaction equation

HRID 1441689 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:11][CH2:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1.Cl.[NH2:26][OH:27].C(N(CC)CC)C.C(OCC)(=O)C>O1CCCC1.CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:26][OH:27])=[NH:18])=[CH:19][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 443297Hydroxyamine hydrochlorideHCID 591645944-[2-(Benzooxazol-2-yl-butyl-amino)-ethyl]-benzonitrile

Product 1

HCID 178449016HCID 178449016, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

290 mg 4-[2-(Benzooxazol-2-yl-butyl-amino)-ethyl]-benzonitrile were dissolved in a mixture of 10 ml tetrahydrofuran and 20 ml methanol. 930 mg hydroxylamine hydrochloride were added followed by the addition of 2.24 ml triethylamine. The reaction mixture was stirred at 65° C. for two hours. The cooled reaction mixture was diluted by the addition of 100 ml ethyl acetate, then washed three times with 40 ml water. The organic layer was dried over MgSO4, then the solvent was removed in vacuo to obtain 280 mg 4-[2-(Benzooxazol-2-yl-butyl-amino)-ethyl]-N-hydroxy-benzamidine as a pale yellow oil.

Workup

  1. customThe cooled reaction mixture
  2. washwashed three times with 40 ml water
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bef0f04c489748a8807e6bf86835fa51
Source dataset
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07655679B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes