Trichloromethanethiol → Tert-butyl 4-(5-chloro-1,2,4-thiadiazol-3-yl)piperazine-1-carboxylate

HRID 2263353노트

반응식

HRID 2263353 반응식
[NH2:1][C:2](=[NH:16])[N:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[Cl:17][C:18]([SH:21])(Cl)Cl.[OH-].[Na+]>ClCCl.O>[Cl:17][C:18]1[S:21][N:1]=[C:2]([N:3]2[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:7][CH2:8]2)[N:16]=1

참가 물질

6

반응물 3

HCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 15197650Tert-butyl 4-carbamimidoylpiperazine-1-carboxylate

생성물 1

HCID 66523695Tert-butyl 4-(5-chloro-1,2,4-thiadiazol-3-yl)piperazine-1-carboxylate수율 59.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 4-[amino(imino)methyl]piperazine-1-carboxylate (1.50 g, 5.67 mmol) and perchloromethyl mercaptan (0.609 ml, 5.67 mmol) in dichloromethane (20 ml) was added dropwise a solution of sodium hydroxide (0.907 g, 22.7 mmol) in water (2.5 ml) under ice-cooling. Then, the reaction mixture was stirred under ice-cooling for 1 hour and at room temperature for 1 hour. The organic layer was separated, washed with water, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give 1.03 g (59.5%) of the desired product as a solid.

후처리

  1. temperaturecooling
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-457bab2709b24d4496d234e6ab42e904
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851473B2

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