Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | 3-Chloro-1-propyne | HCID 12221 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 14133519 | HCID 14133519 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 14580243 | HCID 14580243 | 51.6% |
Reaction Steps
3.0 g of methyl N-methoxycarbonylglycinate were dissolved in 30 ml of N,N-dimethylformamide. Ice-cooling the mixture, 820 g of sodium hydride (60% oil dispersion) were added thereto under a nitrogen atmosphere and stirred for 20 minutes. Then 2.3 g of propargyl chloride were dropped thereto over 10 minutes and further stirred for 40 minutes. The reaction mixture was poured into ice-water and then sodium chloride was added thereto to saturate the same. Thereafter the aqueous layer was washed with hexane and it was subjected to two times of extraction with 100 ml of ether. The ether layers were combined together and dried over anhydrous magnesium sulfate and the solvent was evaporated off to obtain 1.95 g of methyl N-propargyl-N-methoxycarbonylglycinate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04827020 |
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| Source dataset | uspto-grants-1989_05 |
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| ORD ID | ord-1462714f42824de590dc8a3b24e429be |
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| Source note | uspto-grants-1989_05 |
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