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Dimethyl Sulfoxide → Telmisartan

HRID 2363803
Notes
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Reaction equation

HRID 2363803 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 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

Product 1

HCID 65999TelmisartanYield 80%

Reagents, catalysts & solvents 4

HCID 176
Acetic Acid
Solvent
HCID 180AcetoneSolvent
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-99c70cc063544aa992b7306435a3c593
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691999B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes