3-Thiocresol → HCID 15085618, compound

HRID 2248405Notes

Reaction equation

HRID 2248405 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([SH:8])[CH:3]=1.Cl[CH2:10][CH2:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=[O:14].C(N(CC)CC)C>O1CCCC1>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:13](=[O:14])[CH2:12][CH2:11][CH2:10][S:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 79303-ThiocresolHCID 8471TriethylamineHCID 197503-(4-Fluorobenzoyl)propyl chloride

Product 1

HCID 15085618HCID 15085618, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-thiocresol (25.0 g, 0.2 mole) and 4-chloro-4'-fluorobutyrophenone (40.1 g, 0.2 mole) in tetrahydrofuran (200 ml) was treated with triethylamine (22.3 g, 0.22 mole) and refluxed for six hours under nitrogen. The mixture was concentrated in vacuo, and the residue was partitioned between diethyl ether (200 ml) and water (200 ml). The organic layer was washed three times with sodium hydroxide (1N), water, and brine; dried over anhydrous magnesium sulfate, filtered, and concentrated to a pure oil by tlc (n-butyl chloride) to yield the title compound (57.0 g, 99%); IR(nujol): C=O @ 1686 cm-1 ; NMR(CDCl3, TMS): δ2.08(m,2H,CH2), 2.30(s,3H,ArCH3), 3.00(t,2H,CH2 --CO), 3.10(t,2H,S--CH2), 6.9-7.17(m,4H, 1,3-substituted phenyl), [7.10(d of d, 2H) and 7.97(m,2H) p-F-phenyl]; Anal. Calcd. for C17H17FNOS, MW 288.38: C,70.80; H,7.97; S,11.12. Found: C,70.79; H,6.01; S,11.18. Mass spectrum m/e 288,150.

Workup

  1. temperaturerefluxed for six hours under nitrogen
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was partitioned between diethyl ether (200 ml) and water (200 ml)
  4. washThe organic layer was washed three times with sodium hydroxide (1N), water, and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a pure oil by tlc (n-butyl chloride)

Sources & evidence

ORD record
ord-3c3c95cf3f494519814577e440721399
Source dataset
uspto-grants-1991_08
Patent number
US05039706

Reaction notes

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