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Bromotrimethylsilane → [6-Chloro-5-(4-chloro-3-methyl-phenyl)-1H-benzoimidazol-2ylsulfanylmethyl]-phosphonic acid

HRID 2193855
Notes
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Reaction equation

HRID 2193855 reaction equation
C([O:3][P:4]([CH2:9][S:10][C:11]1[NH:15][C:14]2[CH:16]=[C:17]([Cl:28])[C:18]([C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([CH3:27])[CH:21]=3)=[CH:19][C:13]=2[N:12]=1)(=[O:8])[O:5]CC)C.Br[Si](C)(C)C>C(Cl)Cl.C[Si](C)(C)N[Si](C)(C)C>[Cl:28][C:17]1[C:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([CH3:27])[CH:21]=2)=[CH:19][C:13]2[N:12]=[C:11]([S:10][CH2:9][P:4](=[O:3])([OH:8])[OH:5])[NH:15][C:14]=2[CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86657369[6-Chloro-5-(4-chloro-3-methyl-phenyl)-1H-benzoimidazol-2-ylsulfanylmethyl]-phosphonic acid diethyl ester

Product 1

HCID 58422973[6-Chloro-5-(4-chloro-3-methyl-phenyl)-1H-benzoimidazol-2ylsulfanylmethyl]-phosphonic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 13838
Hexamethyldisilazane
Solvent

Procedure

To a solution of [6-Chloro-5-(4-chloro-3-methyl-phenyl)-1H-benzoimidazol-2-ylsulfanylmethyl]-phosphonic acid diethyl ester 12-1 (140 mg, 0.29 mmol) in CH2Cl2 (0.8 mL) and hexamethyldisilazane (0.8 mL) was added bromotrimethylsilane (0.40 mL, 3.0 mmol). After stirring overnight at room temperature, the volatiles were removed from the mixture via a rotary evaporator. The resulting residue was dissolved in EtOAc (2 mL) and filtered through a 0.45 μm syringe filter. The filtrate was evaporated to dryness, and anhydrous MeOH was added. The mixture was triturated by sonication from MeOH to give a suspension of a fine white solid. The solid was isolated by centrifugation followed by decanting the MeOH. The resulting solid was furthered purified by a second trituration in MeOH, and then dried under vacuum at 40° C. overnight to afford the title compound 12-2. LRMS (API-ES) m/e for C15H13Cl2N2O3PS (M+H)+, calcd 403.23. found 403.1. Anal. Calcd for C15H13Cl2N2O3PS: C, 44.68; H, 3.25; N, 6.95. Found: C, 44.44; 1-1, 3.43; N, 6.68.

Workup

  1. customthe volatiles were removed from the mixture via a rotary evaporator
  2. dissolutionThe resulting residue was dissolved in EtOAc (2 mL)
  3. filtrationfiltered through a 0.45 μm syringe
  4. filtrationfilter
  5. customThe filtrate was evaporated to dryness, and anhydrous MeOH
  6. additionwas added
  7. customThe mixture was triturated by sonication from MeOH
  8. customto give
  9. additiona suspension of a fine white solid
  10. customThe solid was isolated by centrifugation
  11. customby decanting the MeOH
  12. customThe resulting solid was furthered purified by a second trituration in MeOH
  13. customdried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-8a33a54f42674f2d8570eb2121158dce
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329914B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes