Ammonium Chloride → HCID 15780555, compound

HRID 21572Notes

Reaction equation

HRID 21572 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13](OS(C(F)(F)F)(=O)=O)=[CH:14][CH:15]=3)[O:10][C:9](=[O:25])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH4+].[Cl-]>CCN(CC)CC.CO.CS(C)=O>[C:9]([C:13]1[CH:12]=[C:11]2[C:16]([C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][C:9](=[O:25])[O:10]2)=[CH:15][CH:14]=1)([O:10][CH3:11])=[O:25]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 157805544-Phenyl-7-trifluoromethanesulfonyloxycoumarin

Product 1

HCID 15780555HCID 15780555, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 4-phenyl-7-trifluoromethanesulfonyloxycoumarin (1.75 g) and tetrakis (triphenylphosphine)palladium (0) (600 mg) in Et3N (1.3 mL), MeOH (15 mL) and DMSO (25 mL) was stirred under an atmosphere of carbon monoxide for 1 hr. at 70° C. The mixture was then poured onto sat. NH4Cl solution, extracted with EtOAc, dried and evaporated. Chromatography on silica gel (30% EtOAc/hexane) yielded the title compound as a solid, m.p. 133°-135° C.

Workup

  1. customat 70° C
  2. extractionextracted with EtOAc
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-383857397557426d9396ead989757b78
Source dataset
uspto-grants-1995_06
Patent number
US05424320

Reaction notes

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