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

HRID 1892538노트

반응식

HRID 1892538 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-51ceb98c13b44343bc69358d44d272e0
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507690B2

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