Diphenyl Ether → Coumarin 6

HRID 1168656Notes

Reaction equation

HRID 1168656 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].CCO[C:12]([C:14]1[C:23](=[O:24])[O:22][C:21]2[C:16](=[CH:17][C:18]3C[CH2:30][CH2:29][N:28]4[C:19]=3[C:20]=2C[CH2:26][CH2:27]4)[CH:15]=1)=O.C1(OC2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:30][CH2:29][N:28]([C:19]1[CH:18]=[CH:17][C:16]2[CH:15]=[C:14]([C:12]3[S:8][C:3]4[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=4)[N:1]=3)[C:23]([O:22][C:21]=2[CH:20]=1)=[O:24])[CH2:27][CH3:26]

Participants

5

Reactant 3

HCID 7583Diphenyl EtherHCID 87132-Aminothiophenol2×HCID 72653Coumarin 3142×

Product 1

HCID 100334Coumarin 6

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The diphenyl analog of coumarin 6 was prepared by the thermal condensation of 2-aminothiophenol with the diphenyl analog of coumarin 314. 7.5 g of the diphenyl analog of coumarin 314 prepared according to Example 1, 2.45 g of 2-aminothiophenol, 15 g diphenyl, and 15 g phenyl ether were placed in a 50 ml round bottom flask and taken to reflux for 30 minutes. After cooling to room temperature, 50 ml of toluene was added and the product was isolated by filtration, washed with ether, dried in vacuum, and recrystallized from methylene chloride/ethyl acetate.

Workup

  1. customwere placed in a 50 ml round bottom flask
  2. temperatureto reflux for 30 minutes
  3. customthe product was isolated by filtration
  4. washwashed with ether
  5. customdried in vacuum
  6. customrecrystallized from methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-b63f094d0e8b40a693e3cc82137bd70c
Source dataset
uspto-grants-2003_09
Patent number
US06627111B2

Reaction notes

Loading…