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

HRID 1892538ノート

反応式

HRID 1892538 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-51ceb98c13b44343bc69358d44d272e0
出典データセット
uspto-grants-2013_08
特許番号
US08507690B2

反応ノート

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