Methanol → HCID 10215908, compound

HRID 2222896Notes

Reaction equation

HRID 2222896 reaction equation
[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13][S:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)=[O:6])#[N:2].BrC1C=CC(S)=CC=1.CO.I([O-])(=O)(=O)=[O:33].[Na+]>O>[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13][S:14]([C:15]1[CH:16]=[CH:17][C:18]([Br:21])=[CH:19][CH:20]=1)=[O:33])=[O:6])#[N:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 660494-BromothiophenolHCID 10215686HCID 10215686, compoundHCID 23667635Sodium periodate

Product 1

HCID 10215908HCID 10215908, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

trans-N-Cyanomethyl-2-(4-bromophenylsulfanylmethyl)cyclohexanecarboxamide (197 mg, 0.536 mmol), prepared as in Example 1 but substituting 4-fluorothiophenol with 4-bromothiophenol, was weighed into a 50 mL round bottom flask fitted with a stirrer and vented cap. Methanol (20 mL) was added to the flask and the reaction mixture was warmed to 50° C. until a clear colorless solution formed. Added sodium periodate (128 mg, 0.599 mmol) solution in water (2.0 mL). A white precipitate slowly formed. The reaction mixture was stirred at 50° C. for 8 h and then concentrated on a rotary evaporator. The residue was triturated in hot water (20 mL) and the reaction mixture was cooled to room temperature. Solids were isolated by filtration, washed thoroughly with water and dried under high vacuum to give trans-N-cyanomethyl-2-(4-bromophenylsulfinylmethyl)cyclohexanecarboxamide as a white solid.

Workup

  1. customwas weighed into a 50 mL round bottom flask
  2. customfitted with a stirrer
  3. customvented cap
  4. customformed
  5. customA white precipitate slowly formed
  6. concentrationconcentrated on a rotary evaporator
  7. customThe residue was triturated in hot water (20 mL)
  8. temperaturethe reaction mixture was cooled to room temperature
  9. customSolids were isolated by filtration
  10. washwashed thoroughly with water
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-829cf3cba3d641eb82e17e0981a8e6f8
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

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