Hydrochloric Acid → 2-chloro-5-nitrobenzenethiol

HRID 1442465ノート

反応式

HRID 1442465 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 47130122-chloro-5-nitrobenzenethiol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-64d10255205a482e90dd35526d24c87c
出典データセット
uspto-grants-2010_02
特許番号
US07658868B2

反応ノート

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