Tetrahydrofuran → [2-Amino-5(4-methoxybenzoyl)phenyl](3-chlorophenyl)-methanone

HRID 1788049Notes

Reaction equation

HRID 1788049 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:9][N:10]=[C:11]3[CH:16]=[CH:15][C:14]([C:17]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)=[O:18])=[CH:13][C:12]=23)[CH:5]=[CH:6][CH:7]=1.C1COCC1>O>[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:18])[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:13][C:12]=1[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)=[O:9]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 17976096[3-(3-Chlorophenyl)-2,1-benzisoxazol-5-yl](4-methoxyphenyl)-methanone

Product 1

HCID 17976112[2-Amino-5(4-methoxybenzoyl)phenyl](3-chlorophenyl)-methanoneYield 104.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Intermediate 10 (0.0536 mol) was added at room temperature to THF (200 ml). TiCl3 15% in water (120 ml) was added dropwise at room temperature. The mixture was stirred at room temperature for 3 hours, poured out into ice water and extracted with DCM. The organic layer was separated, washed with K2CO3 10% then with water, dried (MgSO4), filtered and the solvent was evaporated, yielding 20.5 g (quantitative) of [2-amino-5(4-methoxybenzoyl)phenyl](3-chlorophenyl)-methanone (intermediate 11).

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. washwashed with K2CO3 10%
  4. dry with materialwith water, dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-caaed9f827414c17971404255f2117a8
Source dataset
uspto-grants-2009_03
Patent number
US07511138B2

Reaction notes

Loading…