Chloroacetamide → Deoxy modafinil

HRID 1828393Notes

Reaction equation

HRID 1828393 reaction equation
[Br-].[CH:2]([S:15][C:16](N)=[NH2+])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.ClC[C:21]([NH2:23])=[O:22]>>[CH:2]([S:15][CH2:16][C:21]([NH2:23])=[O:22])([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 6580ChloroacetamideHCID 22066263Benzhydryl thiuronium bromide

Product 1

HCID 9965017Deoxy modafinil

Procedure

In Steps 2 and 3, the S-benzhydrylthiouronium bromide formed in step 1 is converted to the corresponding thiol, and then reacted with chloroacetamide to form 2-(benzhydrylthiyl)acetamide. For example, the thiourea can be converted to the thiol by reaction with a suitable base. The reaction steps 2 and 3 can be carried out in the same reaction vessel as was employed in step 1, without isolation of any intermediates.

Sources & evidence

ORD record
ord-6f51193a1bec450cac8eecea6f36b408
Source dataset
uspto-grants-2006_06
Patent number
US07057069B2

Reaction notes

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