Tetrahydrofuran → HCID 67580135, compound

HRID 1603244Notes

Reaction equation

HRID 1603244 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:15][C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[CH:8]=[CH:7][C:5]=2[CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:22][CH2:23][C:24](Br)=[O:25].C1COCC1>C(Cl)(Cl)Cl.O.CCCCCC>[Br:22][CH2:23][C:24]([N:15]=[C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]1[CH:8]=[CH:7][C:5]1[CH:4]=[CH:3][CH:2]=[CH:1][CH:6]=1)=[O:25]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 9212Dibenz(b,f)azepineHCID 10340Sodium CarbonateHCID 61147Bromoacetyl bromide2×

Product 1

HCID 67580135HCID 67580135, compoundYield 116%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8058HexaneSolvent

Procedure

A solution of 6.0 g (0.03 mole) of iminostilbene in 250 mL of chloroform was added to a solution of 10 g (0.09 mole) of sodium carbonate in 100 mL of water and the mixture was stirred rapidly. To this rapidly stirring solution 6.2 g (0.03 mole) of bromoacetyl bromide was added dropwise through an additional funnel, at which time thin layer chromatography analysis using 2:1 THF:hexane indicated the reaction was incomplete. An additional 1.0 g (0.005 mole) of bromoacetyl bromide was added. Thin layer chromatography indicated that the starting material had been totally consumed. The chloroform layer was separated, dried over Na2SO4 and concentrated to yield 11.0 g of N-bromoacetyliminostilbene (38) as a light yellow oil. This material was used in the following reaction.

Workup

  1. customhad been totally consumed
  2. customThe chloroform layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5b50d886bfe04f929ba6231869ed97c5
Source dataset
uspto-grants-1999_11
Patent number
US05986094

Reaction notes

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