3-ethoxycarbonylmethyl-6-fluoro-5-nitro-2(3H)-benzothiazolone → 5-amino-3-ethoxycarbonylmethyl-6-fluoro-2(3H)-benzothiazolone

HRID 477597

반응식

HRID 477597 반응식
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:11]2[CH:12]=[C:13]([N+:17]([O-])=O)[C:14]([F:16])=[CH:15][C:10]=2[S:9][C:8]1=[O:20])=[O:5])[CH3:2]>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:17][C:13]1[C:14]([F:16])=[CH:15][C:10]2[S:9][C:8](=[O:20])[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:11]=2[CH:12]=1

참가 물질

5

반응물 1

HCID 140142443-ethoxycarbonylmethyl-6-fluoro-5-nitro-2(3H)-benzothiazolone

생성물 1

HCID 140142455-amino-3-ethoxycarbonylmethyl-6-fluoro-2(3H)-benzothiazolone수율 71.7%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 176Acetic Acid용매2회HCID 8857Ethyl Acetate용매

실험 절차

Electrolytic iron powder (0.29 g) was suspended in 5% acetic acid (2 ml), and a solution of 3-ethoxycarbonylmethyl-6-fluoro-5-nitro-2(3H)-benzothiazolone (0.31 g) in acetic acid (1 ml) and ethyl acetate (1 ml) was dropwise added thereto while heating. The resultant mixture was heated under reflux for 3 hours. The reaction mixture was subjected to filtration with celite, and the filtrate was extracted with ethyl acetate. The extract was washed with water and sodium bicarbonate solution, dried and concentrated to give 0.20 g of 5-amino-3-ethoxycarbonylmethyl-6-fluoro-2(3H)-benzothiazolone. m.p., 172.5°-173.5° C.

후처리

  1. temperaturewhile heating
  2. temperatureunder reflux for 3 hours
  3. filtrationThe reaction mixture was subjected to filtration with celite
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe extract was washed with water and sodium bicarbonate solution
  6. customdried
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-74511024267542968a8c318fedce1e25
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04888428

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