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Potassium thiocyanate → (R)-N-benzyl-N-(2-(3-(6,8-difluorochroman-3-yl)-2-thioxo-2,3-dihydro-1H-imidazol-4-yl)ethyl)-2-nitrobenzenesulfonamide

HRID 526725
ノート
印刷プレビュー

反応式

HRID 526725 の反応式
O[C@H]([C@@H](O)C(O)=O)C(O)=O.[F:11][C:12]1[CH:13]=[C:14]2[C:19](=[C:20]([F:22])[CH:21]=1)[O:18][CH2:17][C@H:16]([NH2:23])[CH2:15]2.[CH2:24]([N:31]([CH2:44][CH2:45][C:46](=O)[CH2:47]O)[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N+:41]([O-:43])=[O:42])(=[O:34])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[S-:50][C:51]#[N:52].[K+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.CC(O)C.O.C(O)C>[CH2:24]([N:31]([CH2:44][CH2:45][C:46]1[N:23]([C@@H:16]2[CH2:15][C:14]3[C:19](=[C:20]([F:22])[CH:21]=[C:12]([F:11])[CH:13]=3)[O:18][CH2:17]2)[C:51](=[S:50])[NH:52][CH:47]=1)[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[N+:41]([O-:43])=[O:42])(=[O:34])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 516872Potassium thiocyanateHCID 516892Sodium BicarbonateHCID 25118723(R)-6,8-difluorochroman-3-amine (2R,3R)-2,3-dihydroxysuccinateHCID 71152063N-benzyl-2-nitro-N-(4-hydroxy-3-oxobutyl)benzenesulfonamide2 回

生成物 1

HCID 71152068(R)-N-benzyl-N-(2-(3-(6,8-difluorochroman-3-yl)-2-thioxo-2,3-dihydro-1H-imidazol-4-yl)ethyl)-2-nitrobenzenesulfonamide
収率 64%

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 3776Isopropanol溶媒

反応条件

温度
100 °C

実験手順

To a mixture of (R)-6,8-difluorochroman-3-amine(2R,3R)-2,3-dihydroxysuccinate (compound JT′, 1.7 g, 5.07 mmol), N-benzyl-N-(4-hydroxy-3-oxobutyl)-2-nitrobenzenesulfonamide (compound I, 2.303 g, 6.08 mmol) in acetic acid (12.5 ml) was added potassium thiocyanate (0.591 g, 6.08 mmol) in one portion. The mixture was heated with stirring at 100° C. for 3 hours under HPLC control, cooled to 20° C., diluted with 2-propanol (55 ml), cooled to 0° C., aged for 1 hour. The precipitate collected, washed with cold 2-propanol (55 ml), dried to give 12.54 g. The solid was suspended in a mixture of water (38 ml) and ethanol (EtOH) (19 ml), solid sodium bicarbonate (2.255 g, 26.8 mmol) was added in portions with stirring at 20-25° C., stirred for 30 min. Solid collected, washed with water, dried to give (R)—N-benzyl-N-(2-(3-(6,8-difluorochroman-3-yl)-2-thioxo-2,3-dihydro-1H-imidazol-4-yl)ethyl)-2-nitrobenzenesulfonamide (compound K′, 8.4 g, 14.32 mmol, 64.0% yield).

後処理

  1. temperatureThe mixture was heated
  2. temperaturecooled to 20° C.
  3. temperaturecooled to 0° C.
  4. waitaged for 1 hour
  5. customThe precipitate collected
  6. washwashed with cold 2-propanol (55 ml)
  7. customdried
  8. customto give 12.54 g
  9. additionwas added in portions
  10. stirringwith stirring at 20-25° C.
  11. stirringstirred for 30 min
  12. customSolid collected
  13. washwashed with water
  14. customdried

出典と根拠

ORDレコード
ord-ec3999171d0f43b2a28f78f2420ddff4
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09346751B2

反応ノート

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