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

HRID 493349

반응식

HRID 493349 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
70 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-3bec647fc2294116bc60f4351f38de2b
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534794B2

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