Hydrochloric Acid → 2-chloro-5-nitrobenzenethiol

HRID 721968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 721968
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]C#N.[BH4-].[Na+].Cl>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[SH:11]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 1277678Thiocyanic acid, 2-chloro-5-nitrophenyl esterHCID 4311764Sodium borohydride

Produkt 1

HCID 47130122-chloro-5-nitrobenzenethiol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-chloro-5-nitrophenyl thiocyanate (4.38 g, 20.4 mmole) in dry DMF (70 mL) under inert atmosphere, excess sodium borohydride (1.1 g) was added. The mixture was stirred for half hour and poured over crushed ice. The mixture was acidified with 1 N HCl and left at 0° C. for 1 hr. The precipitate were collected by filtration and redissolved in CH2Cl2. The organic layer was further washed with water and dried with MgSO4. The solvent was removed in vacuo to afford yellow crystals. The product was used in the next step without further purification. 1H NMR (300 MHz, d6-acetone) δ: 8.42 (d, 1H, J=2.7 Hz), 7.98 (dd, 1H, J=8.7, 2.7 Hz), 7.68 (d, 1H, J=8.7 Hz), 5.26 (bs, 1H). 13C NMR (75 MHz, d6-acetone) δ: 147.5, 137.9, 136.4, 131.2, 124.8, 121.7. HR-MS (EI): calcd. for C6H4ClNO2S 189.9646 [M+]. found 189.9646.

Aufarbeitung

  1. additionpoured
  2. customover crushed ice
  3. waitleft at 0° C. for 1 hr
  4. filtrationThe precipitate were collected by filtration
  5. dissolutionredissolved in CH2Cl2
  6. washThe organic layer was further washed with water
  7. dry with materialdried with MgSO4
  8. customThe solvent was removed in vacuo
  9. customto afford yellow crystals
  10. customThe product was used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-a9c9d947838a4f5faa171b075a624ff9
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138075B2

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