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Dimethyl Sulfoxide → Telmisartan

HRID 2363803
ノート
印刷プレビュー

反応式

HRID 2363803 の反応式
[CH3:1][CH2:2][CH2:3][C:4]1[NH:12][C:11]2[C:6](=[C:7]([CH3:23])[CH:8]=[C:9]([C:13]3[N:21]([CH3:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[CH:10]=2)[N:5]=1.[CH3:24]S(C)=O.[OH-].[Na+].C[O:31][C:32]([C:34]1[C:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:36][CH:37]=[C:38](CBr)[CH:39]=1)=[O:33]>CC(C)=O.ClCCl.C(O)(=O)C.O>[CH2:3]([C:4]1[N:12]([CH2:24][C:45]2[CH:44]=[CH:43][C:42]([C:35]3[C:34]([C:32]([OH:31])=[O:33])=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:47][CH:46]=2)[C:11]2[CH:10]=[C:9]([C:13]3[N:21]([CH3:22])[C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[N:14]=3)[CH:8]=[C:7]([CH3:23])[C:6]=2[N:5]=1)[CH2:2][CH3:1]
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 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 97964884-Methyl-6-(1-methyl-1H-benzimidazol-2-yl)-2-propyl-1H-benzimidazoleHCID 19595328Methyl 4-(bromomethyl)(1,1'-biphenyl)-2-carboxylate

生成物 1

HCID 65999Telmisartan収率 80%

試薬・触媒・溶媒 4

HCID 176
Acetic Acid
溶媒
HCID 180Acetone溶媒
HCID 962Water溶媒
HCID 6344Dichloromethane溶媒

反応条件

温度
27.5 °C

実験手順

50 gm of [1H-Benzimidazole-2-n-propyl-4-methyl-6-(1′-methyl benzimidazole-2′-yl)] was added to 200 ml dimethyl sulfoxide and 50 gm of sodium hydroxide. To this was added 60 gm of methyl-4-(bromomethyl)biphenyl-2-carboxylate at ambient temperature. The contents were stirred for 2 hours at 25-30° C. and then heated to 40-50 and maintained for 2 hours. About 500 ml water was added to the reaction mixture and acidified with acetic acid to pH 4.2, extract4ed twice with 250 ml of dichloromethane and the combined extracts were concentrated and isolated by filtration after addition of 300 ml acetone, dried under reduced pressure at 50-60° C. to give 75.0 gm (80%) of the title compound.

後処理

  1. temperatureheated to 40-50
  2. temperaturemaintained for 2 hours
  3. concentrationthe combined extracts were concentrated
  4. customisolated by filtration
  5. customdried under reduced pressure at 50-60° C.

出典と根拠

ORDレコード
ord-99c70cc063544aa992b7306435a3c593
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08691999B2

反応ノート

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