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Triethylamine → HCID 22227943, compound

HRID 1744565
Notes
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Reaction equation

HRID 1744565 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([OH:9])=O)=[CH:5][C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:3]1.[NH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:25][CH2:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[C:21]([CH:24]=1)[C:22]#[N:23].C(N(CC)CC)C.P(C#N)(OCC)(OCC)=O>O.CN(C)C=O>[C:22]([C:21]1[CH:24]=[C:17]([NH:16][C:7]([C:6]2[N:2]([CH3:1])[N:3]=[C:4]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:5]=2)=[O:9])[CH:18]=[CH:19][C:20]=1[O:25][CH2:26][C:27]([CH3:29])([CH3:28])[CH3:30])#[N:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 75376251-Methyl-3-phenyl-1H-pyrazole-5-carboxylic acidHCID 178227345-Amino-2-neopentyloxybenzonitrile

Product 1

HCID 22227943HCID 22227943, compoundYield 19.7%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

1-Methyl-3-phenylpyrazole-5-carboxylic acid (0.8 g), 5-amino-2-neopentyloxybenzonitrile (0.8 g), triethylamine (1.2 g) and diethyl cyanophosphate (1.0 g) were added to dimethylformamide (10 ml) and the mixture was stirred at room temperature for 1 h. The reaction mixture was added into water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. n-Hexane was added to the residue to allow crystallization. The crystals were recrystallized from hydrous methanol to give the title compound (0.3 g), melting point: 223–224° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. additionn-Hexane was added to the residue
  6. customcrystallization
  7. customThe crystals were recrystallized from hydrous methanol

Sources & evidence

ORD record
ord-22f6f32a8864492eab0f3a6d6f08baee
Source dataset
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07015218B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes