Dimethylformamide → 3-[(8-Acetamidoquinoline-5-sulfonyl)methyl]phenyl acetate

HRID 904723

반응식

HRID 904723 반응식
[C:1]([NH:4][C:5]1[C:14]2[N:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]([S:15]([OH:17])=[O:16])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[C:18]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28]Br)[CH:23]=1)(=[O:20])[CH3:19].C(=O)(O)[O-].[Na+].CN(C)C=O>O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([S:15]([CH2:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([O:21][C:18](=[O:20])[CH3:19])[CH:23]=2)(=[O:17])=[O:16])=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[CH:10]2)(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 64220753-(Bromomethyl)phenyl acetateHCID 204310988-Acetamido-5-quinolinesulfinic acid

생성물 1

HCID 204311103-[(8-Acetamidoquinoline-5-sulfonyl)methyl]phenyl acetate

시약·촉매·용매 1

HCID 962Water용매

실험 절차

8-Acetamido-5-quinolinesulfinic acid (10 g, 40 mmole), m-(bromomethyl)phenyl acetate (11 g, 44 mmole), excess sodium bicarbonate (5 g) and dry dimethylformamide (50 ml) were mixed and heated on the steam bath for 11/2 hours. The mixture was slowly poured into 800 ml stirred water and the mixture stirred another 30 min. The solid was filtered off, washed with water, and air-dried overnight. Yield 15.8 g (99 percent) of crude but relatively pure product, m.p. 179°-182° C. A sample recrystallized from toluene, melted 180°-182° C.

후처리

  1. temperatureheated on the steam bath for 11/2 hours
  2. additionThe mixture was slowly poured into 800 ml
  3. filtrationThe solid was filtered off
  4. washwashed with water
  5. customair-dried overnight
  6. customA sample recrystallized from toluene
  7. custommelted 180°-182° C.

출처 및 근거

ORD 기록
ord-abb3f45e76e34738869da91aab2f539b
출처 데이터셋
uspto-grants-1983_12
특허 번호
US04419435

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