1-Bromopentane → HCID 53863338, compound

HRID 1463473Notes

Reaction equation

HRID 1463473 reaction equation
[CH2:1](Br)[CH2:2][CH2:3][CH2:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].[OH:13][C:14]1[CH:15]=[C:16]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH:17]=[CH:18][C:19]1[S:20][C:21]2[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]=2[N:28]=1>CN(C)C=O>[CH3:33][O:32][C:31]1[CH:30]=[CH:29][C:16]([CH:17]=[CH:18][C:19]2[S:20][C:21]3[NH:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]=3[N:28]=2)=[CH:15][C:14]=1[O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 54540894HCID 54540894, compound

Product 1

HCID 53863338HCID 53863338, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Amyl bromide (0.49 ml) and potassium carbonate (0.46 g) were added to a solution (20 ml) of 2-(3-hydroxy-4-methoxy-styryl)-5,6,7,8-tetrahydro-4H-thiazolo[5,4-b]azepine (1.00 g) in dimethylformamide, and the whole was stirred for 1 hr. at 100°. After cooling, the reaction mixture was washed with water, dried and concentrated under reduced pressure. The residue was purified by a column chromatography on silica gel, and recrystallized from isopropyl ether to give the title compound (0.19 g, 15.4%). m.p. 124-125°.

Workup

  1. customat 100°
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a column chromatography on silica gel
  7. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-9166bc06668e41a9b93a4f27f4e6ef55
Source dataset
uspto-grants-1994_04
Patent number
US05300639

Reaction notes

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