Lithium Bromide → HCID 58707374, compound

HRID 450843Notes

Reaction equation

HRID 450843 reaction equation
[NH2:1][C:2]1[C:6]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:12](=[O:23])[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[O:21]C.C[S-].[Na+].[Br-].[Li+]>CN(C=O)C>[NH2:1][C:2]1[C:6]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:12](=[O:23])[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[OH:21]

Participants

5

Reactant 3

HCID 82050Lithium BromideHCID 841469HCID 841469, compoundHCID 4378561Sodium methanethiolate

Product 1

HCID 58707374HCID 58707374, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-amino-5-chloro-2-(2,5-dimethoxybenzoyl)-benzofuran (0.83 g, 2.5 mmol), sodium thiomethoxide (0.44 g, 6.25 mmol) and lithium bromide (0.22 g, 2.5 mmol) in anhydrous DMF (30 ml) is heated at 80° C. for 72 h. The solvent is removed under high vacuum and the residue is dissolved in a mixture of aqueous ammonium chloride and ethyl acetate. The organic phase is washed with brine, dried and evaporated under reduced pressure. Purification of the product on silicagel yields the title compound of m.p. 202-205° C. 1H-NMR (d6-DMSO, 300 MHz): 11.81 (s, 1H); 8.21-8.20 (m, 1H); 7.82-7.80 (m, 1H); 7.66-7.63 (m, 3H); 7.11 (dd, 1H); 6.87 (d, 2H); 3.79 (s, 3H).

Workup

  1. customThe solvent is removed under high vacuum
  2. dissolutionthe residue is dissolved in a mixture of aqueous ammonium chloride and ethyl acetate
  3. washThe organic phase is washed with brine
  4. customdried
  5. customevaporated under reduced pressure
  6. customPurification of the product on silicagel

Sources & evidence

ORD record
ord-efec6a999de34538a91d8d972826df39
Source dataset
uspto-grants-2013_07
Patent number
US08486996B2

Reaction notes

Loading…