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Hydrochloric Acid → N-[2-(3-cyano-1-propen-1-yl)phenylsulfonyl]N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea

HRID 2248949
Notes
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Reaction equation

HRID 2248949 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH3:9])[N:6]=[C:5]([N:10](C2C=CC=CC=2)[C:11](=[O:13])[O-])[N:4]=1.[C:20]([CH2:22][CH:23]=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([NH2:34])(=[O:33])=[O:32])#[N:21].N12CCCCC1C=NCCC2.Cl>O1CCOCC1.O>[C:20]([CH2:22][CH:23]=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31]([NH:34][C:11]([NH:10][C:5]1[N:4]=[C:3]([O:2][CH3:1])[N:8]=[C:7]([CH3:9])[N:6]=1)=[O:13])(=[O:33])=[O:32])#[N:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 199952694-Methoxy-6-methyl-1,3,5-triazin-2-ylphenylcarbamateHCID 540327212-(3-Cyano-1-propen-1-yl)phenylsulfonamide

Product 1

HCID 53795420N-[2-(3-cyano-1-propen-1-yl)phenylsulfonyl]N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaYield 66.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

5.2 g of N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)phenylcarbamate are added to a solution of 4.45 g of 2-(3-cyano-1-propen-1-yl)phenylsulfonamide and 3.3 ml of 1,5-diazabicyclo[5,4,0]undec-5-ene in 80 ml of dioxan, and the mixture is stirred for 15 hours at 20°-25° C. The reaction mixture is then taken up in 350 ml of water and the aqueous solution is acidified to pH 2 with 2N HCl and extracted with ethyl acetate. The organic extracts are combined and concentrated. The oily orange-coloured residue is dissolved in a very small amount of acetone. About 20 ml of diethyl ether are added to this solution, which is diluted dropwise with hexane until the onset of crystallisation. The mixture is subsequently further cooled and the precipitated crystals are isolated by filtration. Yield: 5.2 g of the title compound with a melting point of 142°-143° C.

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationconcentrated
  3. dissolutionThe oily orange-coloured residue is dissolved in a very small amount of acetone
  4. additionAbout 20 ml of diethyl ether are added to this solution, which
  5. additionis diluted dropwise with hexane until the onset of crystallisation
  6. temperatureThe mixture is subsequently further cooled
  7. customthe precipitated crystals are isolated by filtration

Sources & evidence

ORD record
ord-5f5cf593e7224cf0b33b1161e55432e9
Source dataset
uspto-grants-1991_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05041603

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes