Ammonia → Modafinil

HRID 890831Notes

Reaction equation

HRID 890831 reaction equation
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:8][CH2:9][C:10]([NH2:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N.[OH2:20]>ClCCl>[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:8]([CH2:9][C:10]([NH2:12])=[O:11])=[O:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 9965017Deoxy modafinil

Product 1

HCID 4236ModafinilYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 g (38.9 mmoles) of 2-[(diphenylmethyl)thio]acetamide are dissolved in 100 ml of dichloromethane. The solution is added with 15.7 g of 68% w/w ε-phthalimidoperhexanoic acid, keeping the temperature at about 20° C., and after 6 h is diluted with water, adjusting the pH to 8–9 with aqueous ammonia. The resulting phases are separated and the organic one is evaporated to dryness, to obtain 8.5 g of 2-[(diphenylmethyl)sulfinyl]acetamide (modafinil). Molar yield: 80%.

Workup

  1. additionThe solution is added with 15.7 g of 68% w/w ε-phthalimidoperhexanoic acid
  2. customat about 20° C.
  3. customThe resulting phases are separated
  4. customthe organic one is evaporated to dryness

Sources & evidence

ORD record
ord-9c522463d3994dd6baf4150e09fb18d7
Source dataset
uspto-grants-2006_02
Patent number
US06998490B2

Reaction notes

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