Ethyl bromoacetate → HCID 10743970, compound

HRID 1603144Notes

Reaction equation

HRID 1603144 reaction equation
[CH3:1][NH:2][CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:31])[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])=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>C(#N)C>[CH3:1][N:2]([CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([C:14](=[O:31])[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])=[CH:17][CH:16]=2)[CH2:6][CH2:5][CH2:4]1)[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 10716676HCID 10716676, compound

Product 1

HCID 10743970HCID 10743970, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-methylamino-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (1.64 g), acetonitrile (20 ml), potassium carbonate (0.6 g) and ethyl bromoacetate (0.44 ml) is refluxed for 3 hours. The reaction solution is concentrated and water is added to the resulting residue, and the mixture is extracted three times 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; dichloromethane:methanol=30:1), and recrystallized from ethyl acetate/petroleum ether to give 5-(N-methyl-N-ethoxycarbonylmethylamino)-1-[4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.82 g) as colorless prisms, m.p. 167-168° C.

Workup

  1. temperatureis refluxed for 3 hours
  2. concentrationThe reaction solution is concentrated
  3. additionwater is added to the resulting residue
  4. extractionthe mixture is extracted three times with dichloromethane
  5. washThe extract is washed with saturated saline solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. customthe resulting residue is purified by silica gel column chromatography (eluent; dichloromethane:methanol=30:1)
  9. customrecrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-ec5768da61e242dd8b0872c6f4c1cffd
Source dataset
uspto-grants-1999_11
Patent number
US05985869

Reaction notes

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