Phenethyl bromide → HCID 11432173, compound

HRID 1836202Notes

Reaction equation

HRID 1836202 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:18]3[CH2:19][CH2:20][N:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:22][C:17]=3[S:16][C:10]=2[NH:11][C:12](=[O:15])[CH2:13][N:14]=1.[H-].[Na+].Br[CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[Cl-].[NH4+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[C:18]3[CH2:19][CH2:20][N:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:22][C:17]=3[S:16][C:10]=2[N:11]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:12](=[O:15])[CH2:13][N:14]=1

Participants

6

Reactant 4

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 135424453HCID 135424453, compound

Product 1

HCID 11432173HCID 11432173, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

18 g of ethyl 5-(2-chlorophenyl)-1,2,3,6,7,9-hexahydro-2-oxo-8H-pyrido[4′,3′:4,5]thieno[2,3-e]-1,4-diazepine-8-carboxylate (4.46 mmol) is solubilized under argon, in 180 ml of anhydrous dimethylformamide. Sodium hydride at 60% (1.784 g, 4.46 mmol) is added then the reaction medium is heated for approximately 30 minutes at 50° C. until there is no more release. The reaction medium is cooled down to a temperature around 20° C. then 2-bromoethylbenzene (6.2 ml, 4.46 mmol) is added with a syringe. Agitation is carried out for 16 hours at 23° C. then the reaction medium is poured into a saturated solution of ammonium chloride (400 ml). Extraction is carried out with ethyl acetate (2×500 ml). The organic phase is dried over magnesium sulphate then the solvent is evaporated off with a rotary evaporator. After purification by chromatography on a silica column (eluent ethyl acetate-heptane: 0-100 to 20-80), the fractions containing only the product are evaporated and the desired product is obtained in the form of a white amorphous powder (20.3 g, 89%).

Workup

  1. temperatureThe reaction medium is cooled down to a temperature around 20° C.
  2. extractionExtraction
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customthe solvent is evaporated off with a rotary evaporator
  5. customAfter purification by chromatography on a silica column (eluent ethyl acetate-heptane: 0-100 to 20-80)
  6. additionthe fractions containing only the product
  7. customare evaporated

Sources & evidence

ORD record
ord-a287640b41fc432ea93dbec06960d2b9
Source dataset
uspto-grants-2004_08
Patent number
US06777408B1

Reaction notes

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