Ethyl Acetate → N-(3-amino-4-fluorophenyl)-1-chloromethanesulfonamide

HRID 432966노트

반응식

HRID 432966 반응식
[Cl:1][CH2:2][S:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([N+:14]([O-])=O)[CH:8]=1)(=[O:5])=[O:4].C(OCC)(=O)C>C(O)(=O)C.[Fe]>[NH2:14][C:9]1[CH:8]=[C:7]([NH:6][S:3]([CH2:2][Cl:1])(=[O:4])=[O:5])[CH:12]=[CH:11][C:10]=1[F:13]

참가 물질

5

반응물 2

HCID 8857Ethyl AcetateHCID 18760842chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide

생성물 1

HCID 18760845N-(3-amino-4-fluorophenyl)-1-chloromethanesulfonamide수율 94%

시약·촉매·용매 2

HCID 23925Iron촉매HCID 176Acetic Acid용매2회

반응 조건

온도
80 °C

실험 절차

A mixture of 12.5 g of iron powder (223 mmol) and 16 mL of an aqueous solution of acetic acid (8%) was heated to 80° C., and a solution of 6 g of I -chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide (22.3 mmol) in 20 mL of glacial acetic acid and 22 mL ethyl acetate was added dropwise to the mixture. After heating for 1.5 h the reaction mixture was filtered through a pad of Celite® and washed with 200 mL of ethyl acetate and water (twice with 25 mL). The organic phase was separated, dried (MgSO4), filtered and concentrated under reduced pressure to yield 5 g (94%) of the title compound as a solid melting at 128-129° C.

후처리

  1. temperatureAfter heating for 1.5 h the reaction mixture
  2. filtrationwas filtered through a pad of Celite®
  3. washwashed with 200 mL of ethyl acetate and water (twice with 25 mL)
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-bef168359c1344ba9cf349bd425414a3
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664400B2

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