Triethylamine → 4-(5-Azidomethyl-imidazol-1-ylmethyl)-2-(2-chloro-phenoxy)-benzonitrile

HRID 379045Notes

Reaction equation

HRID 379045 reaction equation
Cl.[Cl:2][C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[O:5][C:6]1[CH:13]=[C:12]([CH2:14][N:15]2[C:19]([CH2:20]O)=[CH:18][N:17]=[CH:16]2)[CH:11]=[CH:10][C:7]=1[C:8]#[N:9].C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:38]=[N+:39]=[N-:40].[Na+]>C(Cl)Cl.CN(C=O)C>[N:38]([CH2:20][C:19]1[N:15]([CH2:14][C:12]2[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([O:5][C:4]3[CH:22]=[CH:23][CH:24]=[CH:25][C:3]=3[Cl:2])[CH:13]=2)[CH:16]=[N:17][CH:18]=1)=[N+:39]=[N-:40]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 216970452-(2-Chloro-phenoxy)-4-(5-hydroxymethyl-imidazol-1-ylmethyl)-benzonitrile Hydrochloride

Product 1

HCID 216970744-(5-Azidomethyl-imidazol-1-ylmethyl)-2-(2-chloro-phenoxy)-benzonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-chloro-phenoxy)-4-(5-hydroxymethyl-imidazol-1-ylmethyl)-benzonitrile hydrochloride, as described in Example 15, (0.07 g, 0.186 mmol) in CH2Cl2 (4.0 mL), and triethylamine (0.078 mL, 0.558 mmol) at 0° C. was added methanesulfonyl chloride (0.016 mL, 0.205 mmol). The cooling bath was removed and the mixture was stirred for 1 hr. To this solution was added sodium azide (0.018 g, 0.277 mmol) in DMF (1.0 mL). After 1 hr. the reaction mixture was partitioned between EtOAc and saturated NaHCO3 solution. The EtOAc layer was washed with H2O, brine, and dried (MgSO4). Filtration and concentration in vacuo gave the title product which was used in the next step without further purification.

Workup

  1. customThe cooling bath was removed
  2. waitAfter 1 hr
  3. customthe reaction mixture was partitioned between EtOAc and saturated NaHCO3 solution
  4. washThe EtOAc layer was washed with H2O, brine
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-34bb426638b7435d8d0ce80fe8f84056
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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