Aniline → 3-Aminobenzanilide

HRID 522883

반응식

HRID 522883 반응식
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl.[NH2:33][C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37]([OH:39])=O.C(N(CC)C(C)C)(C)C>CN(C=O)C>[NH2:33][C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:39]

참가 물질

6

반응물 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 30842183-Aminobenzoic acid hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 843473-Aminobenzanilide수율 34.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

HATU (230 mg, 0.605 mmol) and aniline (0.063 mL, 0.691 mmol) was added to a solution of 3-aminobenzoic acid hydrochloride (100 mg, 0.576 mmol) and N,N-diisopropylethylamine (0.217 mL, 1.267 mmol) in 1.5 mL of DMF. The reaction solution was stirred at RT for 3 h. The crude material was purified by reverse-phase preparative HPLC using 0.1% TFA in CH3CN/H2O, gradient 20% to 45%. Desired fractions were collected and the solvents were removed under reduced pressure. The residue was passed through 2 g SCX column and washed by 2M NH3 in MeOH to provide 3-amino-N-phenylbenzamide (42 mg, 0.198 mmol, 34.4% yield) as a light-yellow solid.

후처리

  1. customThe crude material was purified by reverse-phase preparative HPLC
  2. customDesired fractions were collected
  3. customthe solvents were removed under reduced pressure
  4. washwashed by 2M NH3 in MeOH

출처 및 근거

ORD 기록
ord-1bf81f3be6c445a1a476271b1692c707
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334269B2

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