HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl Isocyanate → 3-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-5-yl methylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl Isocyanate | HCID 12228 | — |
| Reactant | 3-[[2-(4-Morpholinyl)ethyl]-amino]-1,2-benzisoxazol-5-ol | HCID 18796461 | — |
| Reactant | acetone MeOH DCM | HCID 21584259 | — |
| Catalyst | Cuprous chloride | HCID 62652 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-5-yl methylcarbamate | HCID 18796447 | 32.9% |
Reaction Steps
To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]-amino]-1,2-benzisoxazol-5-ol (1 g) and a catalytic amount of copper(I)chloride (0.05 g) in EtOAc (100 ml) was added methyl isocyanate (0.26 g). After 24 hours TLC (silica gel, 1:1:20 acetone/MeOH/DCM) showed no starting material. The reaction was filtered through neutral alumina eluting with EtOAc (1 l) and the filtrate was concentrated in vacuo. The residue was further purified by flash chromatography (silica gel) eluting with 1:1:20 acetone/MeOH/DCM to yield 0.4 g of the product, m.p. 135-136° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05925766 |
| Source dataset | uspto-grants-1999_07 |
| ORD ID | ord-3c25173fb72540b2bb1965aa31352bf1 |
| Source note | uspto-grants-1999_07 |