Structurally, this compound is the sulfide (thioether) precursor to modafinil, lacking the sulfoxide oxidation present in the active drug. It serves as the direct substrate for the oxidation step (typically using hydrogen peroxide or another oxidizing agent) that converts the thioether to the sulfinyl group defining modafinil's active pharmacophore. Because it is structurally so close to the final API, it is tightly controlled and quantified as a specified impurity in finished modafinil/armodafinil drug substance.
Diphenylmethyl thioacetamide (2-[(diphenylmethyl)thio]acetamide), also referred to as "Deoxy Modafinil," is a key synthetic intermediate and pharmacopeial-designated impurity in the manufacture of modafinil and armodafinil, wakefulness-promoting agents used to treat narcolepsy and related sleep disorders.
| Chemical Name | Diphenylmethyl Thioacetamide (2-[(Diphenylmethyl)thio]acetamide) |
| CAS Number | 68524-30-1 |
| IUPAC Name | 2-[(Diphenylmethyl)thio]acetamide |
| Molecular Formula | C15H15NOS |
| Molecular Weight | 257.35 g/mol g/mol |
| Boiling Point | 427.7°C at 760 mmHg |
| Density | ~1.18--1.2 g/cm³ |
Direct synthetic precursor requiring oxidation to yield the active pharmaceutical ingredient.
Used as USP Related Compound C / Armodafinil Impurity E for drug substance quality control and impurity profiling.
Applied in process development and route optimization for wakefulness-promoting agent manufacturing.
Reference material for HPLC/impurity method validation in modafinil-related drug product testing.
US Patent 4177290 (foundational synthesis reference)
J. Pharm. Biomed. Anal.
Org. Process Res. Dev.
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