Cyanamide → N-cyano-N'-(3-pyridinyl)thiourea
Reaction equation
[N:1]#[C:2][NH2:3].[H-].[Na+].[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N:12]=[C:13]=[S:14])[CH:7]=1>C1COCC1>[C:2]([NH:3][C:13]([NH:12][C:8]1[CH:7]=[N:6][CH:11]=[CH:10][CH:9]=1)=[S:14])#[N:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of cyanamide (352 mg, 8.40 mmol) in THF (20 mL) at 0° C. was treated with sodium hydride (211 mg of 95% reagent, 8.80 mmol). The slurry was stirred for 30 minutes at 0° C. and treated with a solution of 3-pyridyl isothiocyanate (1.12 g, 8.20 mmol) in THF (8 mL). The cooling bath was removed, and the reaction mixture was stirred for 30 minutes. The reaction was quenched with water (15 mL), poured into ethyl acetate (40 mL), and partitioned. The organic phase was washed with brine (10 mL), dried (Na2SO4), filtered, and concentrated. The residue was dissolved in diethyl ether, treated with HCl (2M solution in diethyl ether), and the resulting precipitate was collected providing 1.06 g of the desired product as an off-white solid.
Workup
- customThe cooling bath was removed
- stirringthe reaction mixture was stirred for 30 minutes
- customThe reaction was quenched with water (15 mL)
- additionpoured into ethyl acetate (40 mL)
- custompartitioned
- washThe organic phase was washed with brine (10 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- dissolutionThe residue was dissolved in diethyl ether
- additiontreated with HCl (2M solution in diethyl ether)
- customthe resulting precipitate was collected
Sources & evidence
- ORD record
- ord-7d2623607e154683bfbd229e98c1c759
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06645968B2
Reaction notes
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