Sodium Bicarbonate → HCID 9907536, compound

HRID 1168461Notes

Reaction equation

HRID 1168461 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:25]=[CH:24][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][C:16]=2[Cl:23])=[O:14])=[C:11]([Cl:26])[CH:10]=1.C([O-])(O)=O.[Na+]>ClCCl>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:25]=[CH:24][C:12]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[Cl:23])=[O:14])=[C:11]([Cl:26])[CH:10]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 9821582HCID 9821582, compound2×

Product 1

HCID 9907536HCID 9907536, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-(2-aminophenylamino)-2,2′-dichloro-4′-methoxybenzophenone (Compound 112) (1.00 g, 2.6 mmol) in dichloromethane (40 ml) was cooled to −78° C. under argon. Borontribromide (1.0 ml, 10.4 mmol) in dichloromethane (5 ml) was added dropwise under stirring. After 15 min the reaction mixture was allowed to come to room temperature over 1 h, and then at 45° C. for 16 hours. The reaction mixture was poured into saturated NaHCO3 and then extracted with EtOAc several times. The organic phases was collected, dried (MgSO4), filtered, and concentrated in vacuo to give the crude product. Concentration in vacuo from a solution of methanol removed traces of boric acid. The crude product was further purified by flash chromatography using EtOAc/pentane 3:2 as eluent.

Workup

  1. waitto come to room temperature over 1 h
  2. waitat 45° C. for 16 hours
  3. extractionextracted with EtOAc several times
  4. customThe organic phases was collected
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7dc1d4569390496f85b0e90f2723621c
Source dataset
uspto-grants-2003_09
Patent number
US06624199B1

Reaction notes

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