Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)- → 2,3,5-Trichloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamide

HRID 23817

반응식

HRID 23817 반응식
[Cl:1][C:2]1[C:14]([Cl:15])=[CH:13][C:12]([Cl:16])=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][CH:8]=[N:9][OH:10])=[O:5].CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.[CH3:38][OH:39].Cl.C([BH3-])#N.[Na+]>CO>[Cl:1][C:2]1[C:14]([Cl:15])=[CH:13][C:12]([Cl:16])=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]([CH:38]=[O:39])[OH:10])=[O:5]

참가 물질

6

반응물 4

HCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 5003444Sodium cyanoborohydrideHCID 21893726Hydrochloride methanol2회HCID 739879012,3,5-trichloro-N-(2-hydroxyimino-ethyl)-benzamide

생성물 1

HCID 225905992,3,5-Trichloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamide수율 32%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a solution of 2,3,5-trichloro-N-(2-hydroxyimino-ethyl)-benzamide (0.85 g, 3.0 mmol ) in MeOH (50 mL) under an argon atmosphere at 0° C. was added methyl orange (trace) followed by a saturated solution of MeOH/HCl until a persistent red color was observed. Sodium cyanoborohydride (0.23 g, 3.65 mmol) was dissolved in MeOH (5 mL) was added sequentially with saturated MeOH/HCl over 0.5 h. The reaction mixture was stirred an additional 1 h and the MeOH was removed in vacuo. The residue was basidified with 10% NaOH and extracted (4×25 mL) with dichloromethane/MeOH (9:1). The combined organic extracts were washed with brine, were dried (NaHCO3) and were concentrated. The residue was diluted with ether/MeOH (9:1) and the precipitate was collected to provide the title compound (0.27 g, 32%) as a white solid. ESMS: M+H=283.

후처리

  1. customthe MeOH was removed in vacuo
  2. extractionextracted (4×25 mL) with dichloromethane/MeOH (9:1)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialwere dried (NaHCO3)
  5. concentrationwere concentrated
  6. additionThe residue was diluted with ether/MeOH (9:1)
  7. customthe precipitate was collected

출처 및 근거

ORD 기록
ord-90150c212a0d4468a4c4d3217e1434c3
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852882B2

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