Formic Acid → 2,3-Dichloro-N-{2-[formyl(Hydroxy)amino]ethyl}benzamide

HRID 23815

반응식

HRID 23815 반응식
C(OC(=O)C)(=O)C.[CH:8]([OH:10])=O.[Cl:11][C:12]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:13]=1[C:14]([NH:16][CH2:17][CH2:18][NH:19][OH:20])=[O:15]>N1C=CC=CC=1>[Cl:11][C:12]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:13]=1[C:14]([NH:16][CH2:17][CH2:18][N:19]([CH:8]=[O:10])[OH:20])=[O:15]

참가 물질

5

반응물 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 121339062,3-dichloro-N-(2-hydroxyamino-ethyl)-benzamide

생성물 1

HCID 98384882,3-Dichloro-N-{2-[formyl(Hydroxy)amino]ethyl}benzamide수율 15%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
0 °C

실험 절차

A mixture of acetic anhydride (5 mL) and formic acid (2.5 mL) was allowed to stand at 55° C. for 2.5 h. After cooling to 0° C., the resulting mixed anhydride was added to a solution of 2,3-dichloro-N-(2-hydroxyamino-ethyl)-benzamide (10.5 g, 42 mmol) in pyridine (50 mL) at 0° C. under an argon atmosphere. The reaction mixture was stirred for 2 h and the pyridine was removed in vacuo. The residue was chased three times with water and three times with MeOH. The residue was partitioned between cold brine/1N HCl and dichloromethane/MeOH (9:1). The aqueous layer was extracted (10×100 mL) with dichloromethane/MeOH (9:1). The combined organic extracts were dried (Na2SO4) and were concentrated. Purification by preparative reverse-phase HPLC provided the title compound (1.8 g, 15%) as a white solid. 1H NMR* (400 MHz, CD3OD): δ 8.35 (s, 0.5H); 7.95 (s, 0.5H); 7.60 (m, 1H); 7.35 (m, 2H); 3.79 (m, 1H); 3.73 (m, 1H); 3.62 (m, 2H). * 1:1 mixture of rotamers. ESMS: M+H=277.

후처리

  1. customthe pyridine was removed in vacuo
  2. customThe residue was partitioned between cold brine/1N HCl and dichloromethane/MeOH (9:1)
  3. extractionThe aqueous layer was extracted (10×100 mL) with dichloromethane/MeOH (9:1)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. concentrationwere concentrated
  6. customPurification by preparative reverse-phase HPLC

출처 및 근거

ORD 기록
ord-b2fccfe5718140e08971eb4aca43e8b1
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852882B2

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