Water → HCID 19607844, compound

HRID 1603121Notes

Reaction equation

HRID 1603121 reaction equation
[CH3:1][N:2]([CH3:34])[CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:33])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[C:17]([O:31]C)[CH:16]=2)[CH2:6][CH2:5][CH2:4]1.B(Br)(Br)Br.O.C(=O)([O-])O.[Na+]>ClCCl>[CH3:34][N:2]([CH3:1])[CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:33])[C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[CH3:29])=[C:17]([OH:31])[CH:16]=2)[CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 19607820HCID 19607820, compound

Product 1

HCID 19607844HCID 19607844, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-dimethylamino-1-[3-methoxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.50 g) in dichloromethane (30 ml) is added dropwise to a solution of 1M boron tribromide in dichloromethane (5.46 ml) at -45° C. After completion of the dropping, the mixture is stirred for 1 day while the temperature of the reaction mixture is gradually raised to room temperature. To the reaction solution is added water and the mixture is neutralized with sodium hydrogen carbonate, and extracted with dichloromethane. The extract is washed with saturated saline solution and dried over magnesium sulfate. The solvent is distilled off and the resulting residue is purified by silica gel column chromatography (eluent; chloroform:methanol=500:1), and recrystallized from methanol/diethyl ether to give 5-dimethylamino-1-[3-hydroxy-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.33 g) as white powder, m.p. 201.5-202.5° C.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract is washed with saturated saline solution
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent is distilled off
  5. customthe resulting residue is purified by silica gel column chromatography (eluent; chloroform:methanol=500:1)
  6. customrecrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-9c2cf4c94eca4b9cbf5ec0d140ef2518
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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