N-bromobutanimide → HCID 21098610, compound

HRID 1351247Notes

Reaction equation

HRID 1351247 reaction equation
[ClH:1].[NH2:2][C:3]1[C:4]2[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[C:5]=2[S:6][CH:7]=1.[Br:13]N1C(=O)CCC1=O>CN(C)C=O>[ClH:1].[NH2:2][C:3]1[C:4]2[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[C:5]=2[S:6][C:7]=1[Br:13]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 21098612HCID 21098612, compound

Product 1

HCID 21098610HCID 21098610, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-Amino-5,6-dihydro-4H-benzo[b]thiophene-7-one hydrochloride (the compound of Preparation Example 6) (1.2 g) in N,N-dimethylformamide (33 mL) was added 1.05 g of N-bromosuccinimide (1.05 g) on an ice bath. After stirring for 30 minutes, the solvent was evaporated at reduced pressure, the pH was adjusted to 10 with an aqueous solution of sodium bicarbonate. After extracting with ethyl acetate, and washing the organic layer with water, drying with anhydrous magnesium sulfate was carried out and the solvent was evaporated at reduced pressure. The residue was dissolved in ethyl acetate, and the pH was brought to 1 by adding 4N hydrochloric acid/ethyl acetate. The resulting solid was collected by filtration, washed with ethyl acetate to provide the title compound (1.55 g) as an ocher solid.

Workup

  1. customthe solvent was evaporated at reduced pressure
  2. extractionAfter extracting with ethyl acetate
  3. washwashing the organic layer with water
  4. dry with materialdrying with anhydrous magnesium sulfate
  5. customthe solvent was evaporated at reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. additionby adding 4N hydrochloric acid/ethyl acetate
  8. filtrationThe resulting solid was collected by filtration
  9. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-61d10a14e3914675a5aee78d3d936765
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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