Benzyl Isothiocyanate → 1-benzyl-S-(2-propenyl)-3-(4-trifluoromethyl-3-pyridylcarbonyl)isothiourea
Reaction equation
[H-].[Na+].[F:3][C:4]([F:15])([F:14])[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[C:11]([NH2:13])=[O:12].[CH2:16]([N:23]=[C:24]=[S:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:26](Br)[CH:27]=[CH2:28]>CN(C)C=O.O.C(OCC)(=O)C>[CH2:16]([NH:23][C:24](=[N:13][C:11]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:5]=1[C:4]([F:3])([F:14])[F:15])=[O:12])[S:25][CH2:28][CH:27]=[CH2:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
Sodium hydride (0.09 g, 60% dispersion in mineral oil) was added to a solution of 4-trifluoromethyl-3-pyridinecarboxamide (0.40 g) in N,N-dimethylformamide at 20° C. and stirred for an hour. Benzyl isothiocyanate (0.31 ml) was added to the mixture and stirred at 20° C. for 2 hours, then allyl bromide (0.30 ml) added with stirring at 20° C. for 5 hours. Ethyl acetate and water were added and the organic phase dried (magnesium sulfate), evaporated and purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (3:1) to give 1-benzyl-S-(2-propenyl)-3-(4-trifluoromethyl-3-pyridylcarbonyl)isothiourea (0.55 g, Compound A-724).
Workup
- stirringstirred at 20° C. for 2 hours
- stirringwith stirring at 20° C. for 5 hours
- dry with materialthe organic phase dried (magnesium sulfate)
- customevaporated
- custompurified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (3:1)
Sources & evidence
- ORD record
- ord-b521be6e6e224edf93b543777d31f41f
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07560456B2
Reaction notes
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