Water → HCID 90197137, compound

HRID 576752Notes

Reaction equation

HRID 576752 reaction equation
C(O[CH:4](OCC)[C:5]#[C:6][C:7]1[C:8](=[O:27])[N:9]([CH2:25][CH3:26])[C:10](=[O:24])[N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C:12]=1[CH3:13])C.[C:31]([C:33]1[CH:38]=[CH:37][C:36]([NH:39][NH2:40])=[CH:35][CH:34]=1)#[N:32].S(=O)(=O)(O)O.O>C(#N)C>[CH2:25]([N:9]1[C:8](=[O:27])[C:7]([C:6]#[C:5]/[CH:4]=[N:40]\[NH:39][C:36]2[CH:37]=[CH:38][C:33]([C:31]#[N:32])=[CH:34][CH:35]=2)=[C:12]([CH3:13])[N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=2)[C:10]1=[O:24])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 5837844-HydrazinobenzonitrileHCID 90197059HCID 90197059, compound

Product 1

HCID 90197137HCID 90197137, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-(3,3-diethoxyprop-1-ynyl)-3-ethyl-6-methyl-1-(3-(trifluoromethyl)phenyl)pyrimidin-2,4(1H,3H)-dione (2.40 g) in acetonitrile (72 ml) were added 4-cyanophenylhydrazine (1.11 g) and concentrated sulfuric acid (0.30 ml) and the resulting mixture was stirred at room temperature for thirty minutes. The resulting mixture was cooled to 0° C. and thereto was added water (140 ml) dropwise, and the solids were collected by filtration and washed with water to afford (Z)-4-(2-(3-(3-ethyl-6-methyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)prop-2-yneylidene)hydrazinyl)benzonitrile (2.50 g) as brown solid.

Workup

  1. temperatureThe resulting mixture was cooled to 0° C.
  2. filtrationthe solids were collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-8294734c57f0406eaea9e841a70f73f9
Source dataset
uspto-grants-2015_05
Patent number
US09040516B2

Reaction notes

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