HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonia → Modafinil
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | (-)-Benzhydrylsulfinylacetate | HCID 19020205 | — |
| Product | Modafinil | HCID 4236 | — |
Reaction Steps
Lafon also disclosed the use of an intermediate, a racemic mixture of benzhydrylsulphinylacetic acid to prepare an isomer of modafinil in U.S. Pat. No. 4,927,855, referring to French patent 2,326,181B. The racemic mixture of the acid was reacted with the (−)-α-methylbenzylamine to provide the (−)-benzhydrylsulphinylacetate of (−)-methylbenzylamine which is acidified with concentrated hydrochloric acid to provide (−)benzyhydrylsulphinylacetic acid. The levo-acid thus produced was then reacted with methylsulfate in water and sodium bicarbonate to provide methyl(−)benzhydrylsulphinylacetate. The acetate was then amidated with ammonia gas to provide (−)benzhydrylsulphinylacetamide.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07345188B2 |
| Source dataset | uspto-grants-2008_03 |
| ORD ID | ord-3e70ead699b74ccd91fc5f019952a6b8 |
| Source note | uspto-grants-2008_03 |