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Triethylamine → HCID 21266099, compound

HRID 566317
Notes
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Reaction equation

HRID 566317 reaction equation
[NH:1]([CH:3]([CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:4]([OH:6])[CH3:5])[NH2:2].C(N(CC)CC)C.[CH3:23][O:24][C:25](OC)=[C:26]([C:29]#[N:30])[C:27]#[N:28]>CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>[NH2:30][C:29]1[N:1]([CH:3]([CH2:7][CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:4]([OH:6])[CH3:5])[N:2]=[C:25]([O:24][CH3:23])[C:26]=1[C:27]#[N:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 110079702-(dimethoxymethylidene)propanedinitrileHCID 21266058HCID 21266058, compound

Product 1

HCID 21266099HCID 21266099, compoundYield 30.5%

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolvent
HCID 887
Methanol
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

4.2 g of 3-hydrazino-2-hydroxy-6-phenylhexane are are dissolved in 20 ml of methanol, and 1.38 ml of triethylamine are added. Then, 1.38 g of 1,1-dimethoxy-2,2-dicyano-ethylene are added. The reaction solution is stirred for 2 hours at approx. 20° C. For work-up, the mixture is diluted with citric acid solution and ethyl acetate and extracted three times with ethyl acetate. The combined ethyl acetate phases are dried with magnesium sulphate and evaporated in vacuo. The evaporation residue is chromatographed on silica gel (Merck Si 60 0.04-0.063 mm) with a cyclohexane/ethyl acetate mixture in a ratio of 4:1 to 1:1. This gives a fraction which, after evaporation in vacuo, affords 0.959 g (=30.5% of theory) of 5-amino-4-cyano-3-methoxy-1-[2-hydroxy-6-phenyl-hex-3-yl]-pyrazole as diastereomer mixture.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialThe combined ethyl acetate phases are dried with magnesium sulphate
  3. customevaporated in vacuo
  4. customThe evaporation residue is chromatographed on silica gel (Merck Si 60 0.04-0.063 mm) with a cyclohexane/ethyl acetate mixture in a ratio of 4:1 to 1:1
  5. customThis gives a fraction which
  6. customafter evaporation in vacuo

Sources & evidence

ORD record
ord-e64f29c49e8a4be69f9fc2976bb6b3f7
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06174884B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes