1,4-Dibromobutane → HCID 19992163, compound

HRID 345304Notes

Reaction equation

HRID 345304 reaction equation
[H-].[Na+].[C:3]1([CH2:9][CH:10]2[C:15]3([CH2:21][C:20](=[O:22])[NH:19][CH2:18][CH2:17][S:16]3(=[O:24])=[O:23])[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:25][CH2:26][CH2:27][CH2:28][CH2:29]Br>CS(C)=O.C(OCC)(=O)C>[C:3]1([CH2:9][CH:10]2[C:15]3([CH2:21][C:20](=[O:22])[N:19]([CH2:29][CH2:28][CH2:27][CH2:26][Br:25])[CH2:18][CH2:17][S:16]3(=[O:23])=[O:24])[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 19992148HCID 19992148, compound

Product 1

HCID 19992163HCID 19992163, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of sodium hydride (30 mg) in dimethylsulfoxide (5 ml) was heated at 60° C. under nitrogen atmosphere. After one hour, 1-phenylmethyl-11-oxo-7-thia-10-azaspiro[5.6]dodecane 7,7-dioxide (0.32 g) and 1,4-dibromobutane (5 ml) were added to the mixture at room temperature. After two hours, the mixture was diluted with ethyl acetate (30 ml) and washed with water (30 ml) and brine (30 ml). The organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified with silica gel column (10 g) (ethyl acetate:hexane=1:1) to give 1-phenylmethyl-10-(4-bromobutyl)-11-oxo-7-thia-10-azaspiro[5.6]dodecane 7,7-dioxide (0.35 g).

Workup

  1. waitAfter two hours
  2. washwashed with water (30 ml) and brine (30 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified with silica gel column (10 g) (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-121b1fd3b0d843fa94a7b7d3fff9ca08
Source dataset
uspto-grants-1991_10
Patent number
US05057513

Reaction notes

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