Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2-Chloroethyl isocyanate | HCID 16035 | — |
| Reactant | (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal | HCID 107526 | — |
| Reactant | Monomethylamine methanol | HCID 57454252 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 54470639 | HCID 54470639 | — |
Reaction Steps
A mixture of 3.6 g of D-glucose and a 10% methylamine-methanol solution is heated at 60° C. for 20 minutes in a sealed tube. The reaction mixture is condensed to dryness under reduced pressure, whereby 3.8 g of 1-methylamino-1-deoxy-D-glucose are obtained as a crude product. 3.8 g of said crude product are dissolved in 40 ml of methanol, and a solution of 2.5 g of 2-chloroethyl isocyanate in 10 ml of tetrahydrofuran is added dropwise thereto at 0° to 5° C. The solution is stirred at the same temperature for 1.5 hours. Then, the reaction solution is condensed under reduced pressure, and a mixture of ethyl acetate and ether is added to the residue. 4.5 g of 1-(2-chloroethyl)-3-methyl-3-D-glucopyranosylurea are thereby obtained as colorless caramel.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04182757 |
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| Source dataset | uspto-grants-1980_01 |
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| ORD ID | ord-cc08a78077bc4c00b580c1a2433f77d2 |
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| Source note | uspto-grants-1980_01 |
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