Carbon tetrabromide → N-(4-{2-[4-(2-bromoethyl)phenyl]ethyl}thiazol-2-yl)acetamide

HRID 1892538Notes

Reaction equation

HRID 1892538 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=2)=[CH:6][CH:5]=1.C(Br)(Br)(Br)[Br:22].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:22][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[N:13]=[C:14]([NH:17][C:18](=[O:20])[CH3:19])[S:15][CH:16]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86227320N-(4-{2-[4-(2-Hydroxyethyl)phenyl]ethyl}thiazol-2-yl)acetamide

Product 1

HCID 86227322N-(4-{2-[4-(2-bromoethyl)phenyl]ethyl}thiazol-2-yl)acetamideYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of N-(4-{2-[4-(2-hydroxyethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (1.452 g, 4.998 mmol) in anhydrous dichloromethane (60 ml) were added carbon tetrabromide (2.001 g, 6.035 mmol) and triphenylphosphine (1.571 g, 5.989 mmol) and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (BW-300SP 10 g, ethyl acetate:hexane=2:3→1:1) to give N-(4-{2-[4-(2-bromoethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (1.553 g, 4.396 mmol, yield 88.0%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (BW-300SP 10 g, ethyl acetate:hexane=2:3→1:1)

Sources & evidence

ORD record
ord-51ceb98c13b44343bc69358d44d272e0
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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