HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Bromobenzaldehyde → Methylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Bromobenzaldehyde | HCID 70741 | — |
| Reactant | 2-[(E)-[1-(2-aminothiazol-4-yl)-2-oxo-2-(2-oxoethylamino)ethylidene]amino]oxy-2-methyl-propanoic acid | HCID 15956689 | — |
| Product | Methylamine | HCID 6329 | — |
| Product | 2-[(E)-[1-(2-aminothiazol-4-yl)-2-oxo-2-(2-oxoethylamino)ethylidene]amino]oxy-2-methyl-propanoic acid | HCID 15956689 | — |
Reaction Steps
The synthesis of alkyne 5 is shown in Scheme 2. Aldehyde 2, though available from Aldrich, is expensive, therefore it can be more economical to prepare it from relatively inexpensive 4-bromobenzaldehyde 1 following a literature procedure as described in Thorand, S. and Krause, N. J. Org. Chem. 1998, 63, 8551. Next, reductive amination of aldehyde 2 with methylamine can afford amine 3, which can be subsequently protected to give methyl carbamate 4. Removal of the trimethylsilyl group (TMS) under basic conditions can yield 5 in 90% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07323562B2 |
| Source dataset | uspto-grants-2008_01 |
| ORD ID | ord-5fc9093d0aff44dd9a22a1337d5a800e |
| Source note | uspto-grants-2008_01 |