Phenol → HCID 86747747, compound

HRID 128562Notes

Reaction equation

HRID 128562 reaction equation
C(N(CC)CC)C.[S:8](/[CH:11]=[CH:12]\[C:13]([OH:15])=[O:14])[C:9]#[N:10].CS(Cl)(=O)=O.[C:21]1(O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CN(C1C=CC=CN=1)C.[K+].[Br-]>C1(C)C=CC=CC=1.C(Cl)Cl.O>[S:8](/[CH:11]=[CH:12]\[C:13]([O:15][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:14])[C:9]#[N:10]

Participants

10

Reactant 6

HCID 996PhenolHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 253877Potassium BromideHCID 53838152-Propenoic acid, 3-thiocyanato-

Product 1

HCID 86747747HCID 86747747, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent5×HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (2.3 g., 0.031 mole) in 5 ml of dry toluene was added dropwise to a stirred, suspension of compound 2 (4.0 g., 0.031 mole) in 30 ml of dry toluene at 0° C. To the resulting solution, methanesulfonyl chloride (3.55 g., 0.031 mole) in 15 ml of dry toluene was added dropwise at 0° C. and stirred for 30 minutes. A solution of phenol (2.9 g., 0.031 mole) and dimethylaminopyridine (DMAP) (3.5 g., 0.028 mole) in 40 ml of dry toluene was added dropwise with stirring at 0° C. The mixture was allowed to warm to room temperature and stirred for an additional 3 hours. The mixture, consisting of yellowish gum in a two-phase mixture with toluene, was diluted with methylene chloride, poured into water and the organic phase was separated. The aqueous phase was extracted with methylene chloride. The combined organic phase was washed with sodium bicarbonate solution, water, dried (MgSO4) and concentrated. The residue was column-chromatographed on silica gel using hexane/ether (4:1) as eluant to give product as white crystals, 2.9 g: mp 79°-83° C.; IR (KBr) 1700, 2175 cm-1.

Workup

  1. stirringwith stirring at 0° C
  2. stirringstirred for an additional 3 hours
  3. customthe organic phase was separated
  4. extractionThe aqueous phase was extracted with methylene chloride
  5. washThe combined organic phase was washed with sodium bicarbonate solution, water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was column-chromatographed on silica gel
  9. customto give product as white crystals, 2.9 g

Sources & evidence

ORD record
ord-6d4051b9bd134fabbd621fd024520a20
Source dataset
uspto-grants-1995_11
Patent number
US05464832

Reaction notes

Loading…