HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl Isocyanate → 3-[[2-(4-Morpholinyl)ethyl]amino]1,2-benzisoxazol-6-yl methylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl Isocyanate | HCID 12228 | — |
| Reactant | Dichloromethane methanol | HCID 21226129 | — |
| Reactant | 3-[[2-(4-Morpholinyl)ethyl]amino]-1,2-benzisoxazol-6-ol | HCID 135815059 | — |
| Catalyst | Cuprous chloride | HCID 62652 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-[[2-(4-Morpholinyl)ethyl]amino]1,2-benzisoxazol-6-yl methylcarbamate | HCID 18796458 | 28.8% |
Reaction Steps
To a stirred solution of 3-[[2-(4-morpholinyl)ethyl]amino]-1,2-benzisoxazol-6-ol (2 g) and copper(I)chloride (0.3 g) in EtOAc (60 ml) was added methyl isocyanate (0.5 g). After 3.5 hours TLC (silica gel, 10% MeOH/DCM) showed no starting material. The reaction was filtered through neutral alumina eluting with EtOAc (2 l) and the filtrate was concentrated in vacuo. Flash column chromatography (silica gel) eluting with 1:1:20 acetone/MeOH/DCM afforded a white solid which was recrystallized from EtOAc/pet. ether to yield 0.7 g of the expected product, m.p. 127°-128° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05756754 |
| Source dataset | uspto-grants-1998_05 |
| ORD ID | ord-2da3b8ffd58c4761a5c1ccff83ca1f2c |
| Source note | uspto-grants-1998_05 |