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

HRID 2263353ノート

反応式

HRID 2263353 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-457bab2709b24d4496d234e6ab42e904
出典データセット
uspto-grants-2010_12
特許番号
US07851473B2

反応ノート

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