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Propyl isocyanate → N-[4-(3,5-dimethylphenyl)-5-(4-pyridyl)-1,3-thiazol-2-yl]-N'-propylurea

HRID 1062640
Notes
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Reaction equation

HRID 1062640 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([NH2:20])[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:21]([N:24]=[C:25]=[O:26])[CH2:22][CH3:23].C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]([NH:20][C:25]([NH:24][CH2:21][CH2:22][CH3:23])=[O:26])[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 61033Propyl isocyanateHCID 516892Sodium BicarbonateHCID 9925734[4-(3,5-Dimethylphenyl)-5-(4-pyridyl)-1,3-thiazol-2-yl)amine

Product 1

HCID 22282315N-[4-(3,5-dimethylphenyl)-5-(4-pyridyl)-1,3-thiazol-2-yl]-N'-propylureaYield 34.9%

Reagents, catalysts & solvents 1

HCID 31374Dimethylacetamide
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of [4-(3,5-dimethylphenyl)-5-(4-pyridyl)-1,3-thiazol-2-yl]amine (0.51 g, 1.8 mmol) in N,N-dimethylacetamide (15 mL) was added propyl isocyanate (0.23 g, 2.67 mmol) and the mixture was stirred at 80° C. for 14 h. To the reaction mixture was poured aqueous sodium hydrogencarbonate solution and the precipitated solid was collected by filtration. The obtained solid was washed with water and dried. The crude crystals were recrystallized from ethanol to give the title compound (0.23 g, yield 33%).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washThe obtained solid was washed with water
  3. customdried
  4. customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-93715bfcf43741739753748eadb632a3
Source dataset
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06962933B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes