HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonia → Modafinil acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Dimethyl Sulfate | HCID 6497 | — |
| Reactant | Modafinil acid | HCID 3085267 | — |
| Reactant | (-)-alpha-Methylbenzylamine (-)-benzhydrylsulphinyl acetate | HCID 68553371 | — |
| Product | Modafinil acid | HCID 3085267 | — |
| Product | HCID 178514057 | HCID 178514057 | — |
Reaction Steps
The (−)-α-methylbenzylamine-(−)-benzhydrylsulphinyl acetate is then converted to (−)-benzhydrylsulphinylacetic acid by acid hydrolysis. The latter is esterified in the presence of dimethyl sulphate and then converted to amide in the presence of ammonia (gas). The (−) or l (laevorotatory) enantiomer of modafinil is obtained through this process with an overall yield of 5.7% in relation to the (±) modafinil acid, calculated on the basis of the yields corresponding to each stage.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08729305B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-adb6faae24044927a310dffeec442885 |
| Source note | uspto-grants-2014_05 |