Formamide → 4-Fluorophenyl-tolylthiomethylformamide

HRID 325099Notes

Reaction equation

HRID 325099 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[CH:4][CH:3]=1.[C:10]1([CH3:17])[C:15]([SH:16])=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH:18]([NH2:20])=[O:19].[C:21]1(C)C=CC=CC=1>CCOC(C)=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:20]([CH2:21][S:16][C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:17])[CH:18]=[O:19])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 713FormamideHCID 1140Toluene2×HCID 87122-ThiocresolHCID 680234-Fluorobenzaldehyde

Product 1

HCID 867501664-Fluorophenyl-tolylthiomethylformamideYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of p-fluorobenzaldehyde (13.1 milliliters (hereinafter mL), 122 millimoles (hereinafter mmol) thiocresol (16.64 grams (hereinafter g), 122 mmol), formamide (15.0 mL, 445 mmol), and toluene (300 mL) were combined and heated to toluene reflux with azeotropic removal of H2O for 18 h. The cooled reaction was diluted with EtOAc (500 mL) and washed with satd aq Na2CO3(3×100 mL), satd aq NaCl (100 mL), dried (Na2SO4), and concentrated. The residue was triturated with petroleum ether, filtered and dried in vacuo to afford 28.50 g of the title compound as a white solid (85%). melting point (hereinafter mp)=119-120°.

Workup

  1. customThe cooled reaction
  2. washwashed with satd aq Na2CO3(3×100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was triturated with petroleum ether
  6. filtrationfiltered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-964569a925c544b4a32f0b1e34724b2b
Source dataset
uspto-grants-2001_04
Patent number
US06222036B1

Reaction notes

Loading…