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Triethylamine → HCID 178423916, compound

HRID 1062802
Notes
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Reaction equation

HRID 1062802 reaction equation
C(O[C:4](=[O:14])[CH:5]([C:12]#[N:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)C.Cl.Cl.[CH2:17]([NH:24][NH2:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:26](N(CC)CC)C>C(O)C.C(OCC)(=O)C>[NH2:13][C:12]1[N:24]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:25]=[C:4]([OH:14])[C:5]=1[C:6]1[CH:7]=[CH:8][C:9]([CH3:26])=[CH:10][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 95298Ethyl phenylcyanoacetateHCID 146540Benzylhydrazine dihydrochloride

Product 1

HCID 178423916HCID 178423916, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857
Ethyl Acetate
Solvent

Procedure

To a stirring suspension of ethyl-2-cyano-2-phenylacetate (10.34 g) and benzylhydrazine dihydrochloride (14.87 g) in ethanol (200 ml) at room temperature was added triethylamine (21.27 ml). The reaction mixture was heated to reflux for 24 hours. The solvent was removed under reduced pressure to yield the crude material as a brown oil. This was re-dissolved in ethyl acetate (100 ml) and washed with water (2×75 ml), then dried (MgSO4) and the solvent removed in vacuo to yield a pale brown oil. This was recrystallised from methanol to yield the title product as pale yellow crystals (2.5 g, ca. 20%)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 hours
  3. customThe solvent was removed under reduced pressure
  4. customto yield the crude material as a brown oil
  5. washwashed with water (2×75 ml)
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customto yield a pale brown oil
  9. customThis was recrystallised from methanol

Sources & evidence

ORD record
ord-0b7b6642ccfe48ad9bedc28e689efd2b
Source dataset
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06962923B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes