Formaldehyde → HCID 23149180, compound

HRID 1983057Notes

Reaction equation

HRID 1983057 reaction equation
[Cl:1][C:2]([Cl:14])([F:13])[S:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[O:15]1CCC[CH2:16]1.C=O>O.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:14][C:2]([Cl:1])([F:13])[S:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH2:16][OH:15])[CH:5]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 23149169HCID 23149169, compound

Product 1

HCID 23149180HCID 23149180, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 2723671Tetrabutylammonium HydroxideSolvent

Procedure

0.50 g of 3-{[dichlorofluoromethyl]thio}-1H-indole was dissolved to 10 ml of tetrahydrofuran. 10 ml of formaldehyde 36% in water and 0.4 ml of tetrabutylammonium hydroxide 10% in water were added to the solution, followed by stirring at room temperature for 30 minutes. Water was added to the reaction mixture, and extracted with MTBE. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain 0.54 g of 3-{[dichlorofluoromethyl]thio}-1H-indole-1-ylmethanol.

Workup

  1. extractionextracted with MTBE
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d6f4f96357a24f72949cbdfc3ecadef0
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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