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

HRID 1363236ノート

反応式

HRID 1363236 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-bb595cff459c4a8084e285714a076a0f
出典データセット
uspto-grants-2011_02
特許番号
US07884109B2

反応ノート

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