Reaction #3839390
Related Literature (1)
openreactiondata ↗doi:10.1039/C8SC04228D
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a33404d07898401ea95796f0982c7079No renderable structure data available
CC(=O)NC#NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | N-cyanoacetamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 5634-51-5 |
| Database ID | 151267 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
N-cyanoacetamide (CAS 5634-51-5) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 151267
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a33404d07898401ea95796f0982c7079Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-12488a68924e4a0cb1365e3c77f18d77Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-fda1f81751914b34b20badb06ef617c4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 159.1 g (1.5 mols) of the sodium salt of acetylcyanamide and 137.8 g (1.5 mols+20% excess) of allyl chloride are reacted in 400 ml of sulfolane for 9 hours and 45 minutes at 70°-127° C. analogously to Example 1, and the mixture is worked up in accordance with Example 1. This gives 121.7 g (65.4% of theory) of a colourless distillate, boiling at 98° C./43 mbar.
Source ID: ord-99eb5e7c234f48768e87b7d4d5af6f0bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 23.3 g (0.2 mol+10% excess) of the sodium salt of acetylcyanamide and 30.5 g (0.2 mol) of vinylbenzyl chloride (technical mixture of isomers containing approx. 40% of the para-component and 60% of the meta-component) are reacted in 100 ml of dimethylformamide for 8 hours at 48°-50° C., when the reaction is complete the mixture is filtered with suction, the filtrate is introduced into 300 g of ice and 500 ml of water while stirring vigorously and the mixture is then extracted with ethyl acetate. The ethyl acetate solution is dried with anhydrous sodium sulfate and filtered with suction, the filtrate is decolourised with active charcoal, the solution is filtered and the filtrate is concentrated in vacuo at 40° C. on a rotary evaporator. The residue is dried to constant weight at 40° C./0.13 mbar. This gives 34.9 g (87.1% of theory) of a brownish, viscous liquid, which is purified by bulb tube distillation at 130°-145° C./0.7 mbar. containing approx. 40% of the para-component and 60% of the meta-component) is filtered with suction the filtrate is introduced into 300 g of ice and 500 ml of water the mixture is then extracted with ethyl acetate The ethyl acetate solution is dried with anhydrous sodium sulfate filtered with suction the solution is filtered the filtrate is concentrated in vacuo at 40° C. on a rotary evaporator The residue is dried to constant weight at 40° C./0.13 mbar This gives 34.9 g (87.1% of theory) of a brownish, viscous liquid, which is purified by bulb tube distillation at 130°-145° C./0.7 mbar
Source ID: ord-5935d9e88c544478962797d5696cf3e5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 159.1 g (1.5 mols) of the sodium salt of acetylcyanamide and 137.8 g (1.5 mols+20% excess) of allyl chloride are reacted in 400 ml of sulfolane for 9 hours and 45 minutes at 70°-127° C. analogously to Example 1, and the mixture is worked up in accordance with Example 1. This gives 121.7 g (65.4% of theory) of a colourless distillate, boiling at 98° C./43 mbar.
Source ID: ord-99eb5e7c234f48768e87b7d4d5af6f0bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 23.3 g (0.2 mol+10% excess) of the sodium salt of acetylcyanamide and 30.5 g (0.2 mol) of vinylbenzyl chloride (technical mixture of isomers containing approx. 40% of the para-component and 60% of the meta-component) are reacted in 100 ml of dimethylformamide for 8 hours at 48°-50° C., when the reaction is complete the mixture is filtered with suction, the filtrate is introduced into 300 g of ice and 500 ml of water while stirring vigorously and the mixture is then extracted with ethyl acetate. The ethyl acetate solution is dried with anhydrous sodium sulfate and filtered with suction, the filtrate is decolourised with active charcoal, the solution is filtered and the filtrate is concentrated in vacuo at 40° C. on a rotary evaporator. The residue is dried to constant weight at 40° C./0.13 mbar. This gives 34.9 g (87.1% of theory) of a brownish, viscous liquid, which is purified by bulb tube distillation at 130°-145° C./0.7 mbar. containing approx. 40% of the para-component and 60% of the meta-component) is filtered with suction the filtrate is introduced into 300 g of ice and 500 ml of water the mixture is then extracted with ethyl acetate The ethyl acetate solution is dried with anhydrous sodium sulfate filtered with suction the solution is filtered the filtrate is concentrated in vacuo at 40° C. on a rotary evaporator The residue is dried to constant weight at 40° C./0.13 mbar This gives 34.9 g (87.1% of theory) of a brownish, viscous liquid, which is purified by bulb tube distillation at 130°-145° C./0.7 mbar
Source ID: ord-5935d9e88c544478962797d5696cf3e5Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 159.1 g (1.5 mols) of the sodium salt of acetylcyanamide and 137.8 g (1.5 mols +20% excess) of allyl chloride are reacted in 400 ml of sulfolane for 9 hours and 45 minutes at 70°-127° C. analogously to Example 1, and the mixture is worked up in accordance with Example 1. This gives 121.7 g (65.4% of theory) of a colourless distillate, boiling at 98° C./43 mbar.
Source ID: ord-ec34534ab55944e6bd5e9adb5a5287c2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 23.3 g (0.2 mol +10% excess) of the sodium salt of acetylcyanamide and 30.5 g (0.2 mol) of vinylbenzyl chloride (technical mixture of isomers containing approx. 40% of the para-component and 60% of the meta-component) are reacted in 100 ml of dimethylformamide for 8 hours at 48°-50° C., when the reaction is complete the mixture is filtered with suction, the filtrate is introduced into 300 g of ice and 500 ml of water while stirring vigorously and the mixture is then extracted with ethyl acetate. The ethyl acetate solution is dried with anhydrous sodium sulfate and filtered with suction, the filtrate is decolourised with active charcoal, the solution is filtered and the filtrate is concentrated in vacuo at 40° C. on a rotary evaporator. The residue is dried to constant weight at 40° C./0.13 mbar. This gives 34.9 g (87.1% of theory) of a brownish, viscous liquid, which is purified by bulb tube distillation at 130°-145° C./0.7 mbar. containing approx. 40% of the para-component and 60% of the meta-component) is filtered with suction the filtrate is introduced into 300 g of ice and 500 ml of water the mixture is then extracted with ethyl acetate The ethyl acetate solution is dried with anhydrous sodium sulfate filtered with suction the solution is filtered the filtrate is concentrated in vacuo at 40° C. on a rotary evaporator The residue is dried to constant weight at 40° C./0.13 mbar This gives 34.9 g (87.1% of theory) of a brownish, viscous liquid, which is purified by bulb tube distillation at 130°-145° C./0.7 mbar
Source ID: ord-961aef875ae7459ea50882cc136e09e1Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 159.1 g (1.5 mols) of the sodium salt of acetylcyanamide and 137.8 g (1.5 mols +20% excess) of allyl chloride are reacted in 400 ml of sulfolane for 9 hours and 45 minutes at 70°-127° C. analogously to Example 1, and the mixture is worked up in accordance with Example 1. This gives 121.7 g (65.4% of theory) of a colourless distillate, boiling at 98° C./43 mbar.
Source ID: ord-ec34534ab55944e6bd5e9adb5a5287c2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 23.3 g (0.2 mol +10% excess) of the sodium salt of acetylcyanamide and 30.5 g (0.2 mol) of vinylbenzyl chloride (technical mixture of isomers containing approx. 40% of the para-component and 60% of the meta-component) are reacted in 100 ml of dimethylformamide for 8 hours at 48°-50° C., when the reaction is complete the mixture is filtered with suction, the filtrate is introduced into 300 g of ice and 500 ml of water while stirring vigorously and the mixture is then extracted with ethyl acetate. The ethyl acetate solution is dried with anhydrous sodium sulfate and filtered with suction, the filtrate is decolourised with active charcoal, the solution is filtered and the filtrate is concentrated in vacuo at 40° C. on a rotary evaporator. The residue is dried to constant weight at 40° C./0.13 mbar. This gives 34.9 g (87.1% of theory) of a brownish, viscous liquid, which is purified by bulb tube distillation at 130°-145° C./0.7 mbar. containing approx. 40% of the para-component and 60% of the meta-component) is filtered with suction the filtrate is introduced into 300 g of ice and 500 ml of water the mixture is then extracted with ethyl acetate The ethyl acetate solution is dried with anhydrous sodium sulfate filtered with suction the solution is filtered the filtrate is concentrated in vacuo at 40° C. on a rotary evaporator The residue is dried to constant weight at 40° C./0.13 mbar This gives 34.9 g (87.1% of theory) of a brownish, viscous liquid, which is purified by bulb tube distillation at 130°-145° C./0.7 mbar
Source ID: ord-961aef875ae7459ea50882cc136e09e1Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a33404d07898401ea95796f0982c7079PubChem References
These sources are listed in the compound's public database record.
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