Sodium Chloride → N1-(tert-Butoxycarbonyl)-4-fluoro-1,2-phenylenediamine

HRID 1363236노트

반응식

HRID 1363236 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([N+:16]([O-])=O)[CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C1COCC1.O.CO>[NH2:16][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14]

참가 물질

8

반응물 4

HCID 5234Sodium ChlorideHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 59705030(4-Fluoro-2-nitro-phenyl)-carbamic acid tert-butyl ester

생성물 1

HCID 24688763N1-(tert-Butoxycarbonyl)-4-fluoro-1,2-phenylenediamine

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl 4-fluoro-2-nitrophenylcarbamate (0.34 g) in THF (30 mL) was added a premixed solution of sodium hydrosulfite (2 g) and sodium bicarbonate (1 g) in water (50 mL). MeOH (10 mL) was also added to aid solution of the mixture, which was stirred at room temperature for 30 min, when sodium chloride was added to saturate the solution. The resultant mixture was extracted with EtOAc (2×). The combined organics were dried, filtered and evaporated to yield the titled compound (quant) that was used as such for the next step. 1H-NMR (300 MHz, CDCl3) δ 7.5 (dd, 1H), 6.6 (dd, 1H), 6.5 (m, 1H), 6.4 (br 1H), 4.7 (br 2H), 1.5 (s, 9H); 19F δ −119 ppm; MH+=227 (minor) 127 (-BOC), 171 (-tBu).

후처리

  1. concentrationto saturate the solution
  2. extractionThe resultant mixture was extracted with EtOAc (2×)
  3. customThe combined organics were dried
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-bb595cff459c4a8084e285714a076a0f
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884109B2

반응 노트

불러오는 중…