Ethyl isocyanate → N-Ethyl-N'-{4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-yl}urea

HRID 1727379Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To A solution of 4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]-2-pyridylamine (0.50 g, 1.7 mmol) in N,N-dimethylacetamide (10 mL) was added ethyl isocyanate (0.20 mL, 2.5 mmol) and the reaction mixture was stirred at 80° C. for 20 hours. The reaction mixture was poured into aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The extracts were washed with aqueous sodium hydrogen carbonate solution and brine. The resulting solution was dried, and concentrated under reduced pressure. The obtained crude crystal was recrystallized from ethyl acetate-hexane to give a title compound (0.29 g, yield 47%).

Workup

extractionextracted with ethyl acetate
washThe extracts were washed with aqueous sodium hydrogen carbonate solution and brine
customThe resulting solution was dried
concentrationconcentrated under reduced pressure
customThe obtained crude crystal
customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record: ord-76d33b44456c4b958add8966e1ac0a71
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495018B2

Reaction notes

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