Sodium Hydroxide → 1-(4-Chloro-[1,2,5]thiadiazol-3-yl)piperazine hydrochloride

HRID 493349

反応式

HRID 493349 の反応式
[Cl:1][C:2]1[C:6](Cl)=[N:5][S:4][N:3]=1.O.O.O.O.O.O.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.[OH-].[Na+]>CN(C=O)C.[Cl-].[Na+].O>[ClH:1].[Cl:1][C:2]1[C:6]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[N:5][S:4][N:3]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 798043,4-Dichloro-1,2,5-thiadiazoleHCID 120181Piperazine, hexahydrate

生成物 1

HCID 212020421-(4-Chloro-[1,2,5]thiadiazol-3-yl)piperazine hydrochloride収率 89%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
70 °C

実験手順

A mixture of 3,4-dichloro-1,2,5-thiadiazole (4.00 g, 25.8 mmol) and piperazine hexahydrate (25.0 g, 130 mmol) in DMF (25 mL) was heated at 70° C. for 20 minutes. After cooling to ambient temperature, the reaction mixture was basified (11 M NaOH) and brine was added. The resulting mixture was extracted with CHCl3 (×3). The combined organic phases were washed twice with brine/water (1:1), dried (MgSO4) and the solvent was evaporated. The resulting oil was purified by column chromatography on silica gel using CHCl3 as eluent to give 2.77 g (52%) of the title compound as a colourless oil which was converted to its hydrochloride salt: mp 231° C. (dec). Anal (C6H9ClN4S.HCl), C calc 29.89, found 30.4. H. N

後処理

  1. temperatureAfter cooling to ambient temperature
  2. additionwas added
  3. extractionThe resulting mixture was extracted with CHCl3 (×3)
  4. washThe combined organic phases were washed twice with brine/water (1:1)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated
  7. customThe resulting oil was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-3bec647fc2294116bc60f4351f38de2b
出典データセット
uspto-grants-2009_05
特許番号
US07534794B2

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