4-Bromobenzyl bromide → HCID 118863939, compound

HRID 1485642Notes

Reaction equation

HRID 1485642 reaction equation
[NH:1]=[S:2]([CH3:9])([N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1)=[O:3].[H-].[K+].[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1>COCCOC.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:1]=[S:2]([CH3:9])(=[O:3])[N:4]2[CH2:8][CH2:7][CH2:6][CH2:5]2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 685274-Bromobenzyl bromideHCID 82127Potassium hydrideHCID 10081144HCID 10081144, compound

Product 1

HCID 118863939HCID 118863939, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Imino(methyl)pyrrolidin-1-yl-λ6-sulfanone (80 mg) is added to potassium hydride (87 mg) in 1,2-dimethoxyethane (2 mL) under an argon atmosphere and the resulting mixture is stirred for 15 min at room temperature. Benzyltriethylammonium chloride (7 mg) and 4-bromobenzyl bromide (148 mg) are added and the mixture is stirred overnight at room temperature. The reaction mixture is cooled in an ice bath and quenched with saturated aqueous NH4Cl solution. The mixture is diluted with diethyl ether and extracted with 3 N hydrochloric acid. The aqueous phase is carefully neutralized with solid K2CO3 and extracted with dichloromethane. The combined organic phases are dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel (ethyl acetate/methanol 98:2→90:10) to give the title compound. LC (method 1): tR=0.85 min; Mass spectrum (ESI+): m/z=317, 319 [M+H]+.

Workup

  1. stirringthe mixture is stirred overnight at room temperature
  2. temperatureThe reaction mixture is cooled in an ice bath
  3. customquenched with saturated aqueous NH4Cl solution
  4. additionThe mixture is diluted with diethyl ether
  5. extractionextracted with 3 N hydrochloric acid
  6. extractionextracted with dichloromethane
  7. dry with materialThe combined organic phases are dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue is chromatographed on silica gel (ethyl acetate/methanol 98:2→90:10)

Sources & evidence

ORD record
ord-5412307de8064e76ac693f0a885fe535
Source dataset
uspto-grants-2016_08
Patent number
US09422312B2

Reaction notes

Loading…