Hexamethylphosphoramide → 4-hydroxy-3-(phenylsulfanyl)-2H-chromen-2-one

HRID 2413328

Reaction equation

HRID 2413328 reaction equation
CN(C)P(=O)(N(C)C)N(C)C.Br[C:13]1[C:14](=[O:24])[O:15][C:16]2[C:21]([C:22]=1[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=2.[C:25]1([S:31][Si](C)(C)C)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(#N)C>[C:25]1([S:31][C:13]2[C:14](=[O:24])[O:15][C:16]3[C:21]([C:22]=2[OH:23])=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 12679HexamethylphosphoramideHCID 78312PhenylthiotrimethylsilaneHCID 546821243-bromo-4-hydroxy-2H-chromen-2-one

Product 1

HCID 546846444-hydroxy-3-(phenylsulfanyl)-2H-chromen-2-oneYield 70.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1 ml of hexamethylphosphoric triamide and 1.0 g (4.15 mmoles) of 3-bromo-4-hydroxycoumarin were added to a solution of 0.91 g (5.0 mmoles) of phenylthio(trimethyl)silane in 25 ml of dry acetonitrile. After refluxing for 1 hour, the mixture was evaporated and the residue was dissolved in 125 ml of ethyl acetate. The solution obtained was washed twice with 125 ml of water and the ethyl acetate layer was dried and evaporated to dryness. The solid residue was washed with 100 ml of heptane and then with three portions of 50% ethanol, was vacuum dried at 40° C. to obtain 0.79 g (70.5% yield) of 3-phenylthio-4-hydroxycoumarin melting at 186°-189° C.

Workup

  1. temperatureAfter refluxing for 1 hour
  2. customthe mixture was evaporated
  3. dissolutionthe residue was dissolved in 125 ml of ethyl acetate
  4. customThe solution obtained
  5. washwas washed twice with 125 ml of water
  6. dry with materialthe ethyl acetate layer was dried
  7. customevaporated to dryness
  8. washThe solid residue was washed with 100 ml of heptane
  9. customdried at 40° C.

Sources & evidence

ORD record
ord-e41b81b9509f472eb1d49757b376fbb9
Source dataset
uspto-grants-1985_01
Patent number
US04496720

Linked notes

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