Diisopropylethylamine → tert-Butyl 2-(2-fluoro-4-nitrobenzoyl)-2-methylhydrazinecarboxylate

HRID 56608

반응식

HRID 56608 반응식
F[B-](F)(F)F.N1(O[C+](N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[F:32][C:33]1[CH:41]=[C:40]([N+:42]([O-:44])=[O:43])[CH:39]=[CH:38][C:34]=1[C:35]([OH:37])=O.[CH3:45][NH:46][NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49]>CN(C=O)C>[F:32][C:33]1[CH:41]=[C:40]([N+:42]([O-:44])=[O:43])[CH:39]=[CH:38][C:34]=1[C:35]([N:46]([CH3:45])[NH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])=[O:37]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 3026792-Fluoro-4-nitrobenzoic acidHCID 15671306N'-methyl(tert-butoxy)carbohydrazideHCID 178484679HCID 178484679, 화합물

생성물 1

HCID 117622795tert-Butyl 2-(2-fluoro-4-nitrobenzoyl)-2-methylhydrazinecarboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Under argon and at RT, 17.1 g (53.4 mmol, 1.3 eq.) of (benzotriazol-1-yloxy)bisdimethylaminomethylium fluoroborate and 21.4 ml (123.1 mol, 3.0 eq.) of N,N-diisopropylethylamine were added to a solution of 9.1 g (49.3 mmol, 1.2 eq.) of 2-fluoro-4-nitrobenzoic acid in 200 ml of DMF, and the mixture was stirred at RT for 20 min. A solution of 12.5 g (purity 48%, 41 mmol) of tert-butyl 2-methylhydrazinecarboxylate in 50 ml of DMF was added, and the reaction mixture was stirred at RT for 6 h. After removal of the DMF under reduced pressure and addition of water/ethyl acetate and phase separation, the organic phase was washed with 10% aqueous citric acid and with saturated aqueous sodium chloride solution, dried (sodium sulphate), filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate mixtures). Yield: 8.35 g (65% of theory)

후처리

  1. stirringthe reaction mixture was stirred at RT for 6 h
  2. customAfter removal of the DMF
  3. additionunder reduced pressure and addition of water/ethyl acetate and phase separation
  4. washthe organic phase was washed with 10% aqueous citric acid and with saturated aqueous sodium chloride solution
  5. dry with materialdried (sodium sulphate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by flash chromatography (silica gel 60, mobile phase: cyclohexane/ethyl acetate mixtures)

출처 및 근거

ORD 기록
ord-66727fb3bd2e4db498f2326358c3bab4
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434690B2

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