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Water → 1-((3R)-6,8-Difluoro-3,4-dihydro-2H-1-benzopyran-3-yl)-1,3-dihydro-5-(2-((phenylmethyl)amino)ethyl)-2H-imidazole-2-thione

HRID 526726
ノート
印刷プレビュー

反応式

HRID 526726 の反応式
[CH2:1]([N:8]([CH2:21][CH2:22][C:23]1[N:24]([C@@H:29]2[CH2:38][C:37]3[C:32](=[C:33]([F:40])[CH:34]=[C:35]([F:39])[CH:36]=3)[O:31][CH2:30]2)[C:25](=[S:28])[NH:26][CH:27]=1)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.SCC(O)=O.[OH-].[K+].O>CN(C)C=O.CO.O>[CH2:1]([NH:8][CH2:21][CH2:22][C:23]1[N:24]([C@@H:29]2[CH2:38][C:37]3[C:32](=[C:33]([F:40])[CH:34]=[C:35]([F:39])[CH:36]=3)[O:31][CH2:30]2)[C:25](=[S:28])[NH:26][CH:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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

7

反応物 4

HCID 962WaterHCID 1133Thioglycolic AcidHCID 14797Potassium HydroxideHCID 71152068(R)-N-benzyl-N-(2-(3-(6,8-difluorochroman-3-yl)-2-thioxo-2,3-dihydro-1H-imidazol-4-yl)ethyl)-2-nitrobenzenesulfonamide

生成物 1

HCID 250526301-((3R)-6,8-Difluoro-3,4-dihydro-2H-1-benzopyran-3-yl)-1,3-dihydro-5-(2-((phenylmethyl)amino)ethyl)-2H-imidazole-2-thione収率 91%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 22242641Methanol--water (1/1)溶媒

反応条件

温度
22.5 °C

実験手順

To a solution of (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 g, 13.64 mmol) and 2-mercaptoacetic acid (2.84 ml, 40.9 mmol) in dimethylformamide (DMF) (80 ml) was added 10N potassium hydroxide (10.23 ml, 102 mmol) in one portion with water cooling and the mixture was stirred at 20-25° C. under HPLC control for 3 hours. Methanol-water 1:1 (160 ml) was slowly added with stirring, the mixture was stirred for 2 hours at 20-25° C. Precipitate was collected, washed with MeOH-water 1:1 (80 ml), dried to give (R)-5-(2-(benzylamino)ethyl)-1-(6,8-difluorochroman-3-yl)-1H-imidazole-2(3H)-thione (4.96 g, 12.35 mmol, 91% yield).

後処理

  1. stirringwith stirring
  2. stirringthe mixture was stirred for 2 hours at 20-25° C
  3. customPrecipitate was collected
  4. washwashed with MeOH-water 1:1 (80 ml)
  5. customdried

出典と根拠

ORDレコード
ord-6d5404eec536408196cb9e5a97d7dc55
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

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート