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Water → HCID 178517471, compound

HRID 2389810
Notes
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Reaction equation

HRID 2389810 reaction equation
[C:1]([CH:3]=[C:4]([NH:15][C:16](=[O:20])OCC)[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)#[N:2].[N:21]1([CH2:27][C:28]([NH:30][NH2:31])=O)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(OCC)(=O)C.O>CN1C(=O)CCC1>[N:21]1([CH2:27][C:28]2[N:2]=[C:1]3[N:31]([C:16]([OH:20])=[N:15][C:4]([C:5]4[CH:6]=[CH:7][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:9][CH:10]=4)=[CH:3]3)[N:30]=2)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 3516352-(4-Morpholinyl)acetohydrazideHCID 76754610Ethyl {2-cyano-1-[4-(trifluoromethyl)phenyl]ethenyl}carbamate

Product 1

HCID 178517471HCID 178517471, compound

Reagents, catalysts & solvents 1

HCID 13387
N-methyl-2-pyrrolidone
Solvent

Conditions

Temperature
190 °C

Procedure

2.4 g (8.4 mmol) of ethyl {2-cyano-1-[4-(trifluoromethyl)phenyl]ethenyl}carbamate (Example 129A) and 1.34 g (8.4 mmol) of 2-morpholin-4-ylacetohydrazide are dissolved in NMP (12 ml) and stirred in a flask with a calcium chloride drying tube at an oil-bath temperature of 190° C. for 4 h. The reaction mixture is cooled to RT and ethyl acetate (150 ml) and water (100 ml) are added. The organic phase is washed with saturated sodium bicarbonate solution, separated off, dried with magnesium sulphate and concentrated. The residue is chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 1:1, then with dichloromethane/methanol 100:1). 850 mg (26% of theory) of the product are obtained.

Workup

  1. temperatureThe reaction mixture is cooled to RT
  2. washThe organic phase is washed with saturated sodium bicarbonate solution
  3. customseparated off
  4. dry with materialdried with magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel (mobile phase cyclohexane/ethyl acetate 10:1 to 1:1
  7. custom850 mg (26% of theory) of the product are obtained

Sources & evidence

ORD record
ord-9060d52338e14955b4cb88ca85c6ff58
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08273752B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes