Triethylamine → Ammonium hydroxide methanol

HRID 379032Notes

Reaction equation

HRID 379032 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C([N:13](CC)CC)C.CS(Cl)(=O)=O.[OH:23][C:24]1[CH:31]=[C:30]([CH2:32][N:33]2[CH:37]=[CH:36][N:35]=[CH:34]2)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27].[C:38](=O)([O-])[O-:39].[Cs+].[Cs+]>C(Cl)Cl.CN(C=O)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]([O:23][C:24]2[CH:31]=[C:30]([CH2:32][N:33]3[CH:37]=[CH:36][N:35]=[CH:34]3)[CH:29]=[CH:28][C:25]=2[C:26]#[N:27])[CH3:7])=[CH:9][CH:10]=1.[CH3:38][OH:39].[NH4+:13].[OH-:8]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 31297Methanesulfonyl chlorideHCID 74647p-Chlorophenethylic alcoholHCID 216970282-Hydroxy-4-imidazol-1-ylmethyl-benzonitrile

Product 2

HCID 21697126HCID 21697126, compoundHCID 21894508Ammonium hydroxide methanolYield 0.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

4-chlorophenethyl alcohol (0.11 g, 0.67 mmol) and triethylamine (0.37 mL, 2.68 mmol) were dissolved in CH2Cl2 (5 mL) at 0° C. Then it was treated with methanesulfonyl chloride (0.207 mL, 2.68 mmol), with stirring and warming to ambient temperature, until the indicated loss of starting material. The reaction mixture was concentrated in vacuo, then dissolved in DMF (1 mL) and added to a mixture of 2-hydroxy-4-imidazol-1-ylmethyl-benzonitrile (0.10 g, 0.50 mmol) and cesium carbonate (0.33 g, 1.0 mmol) in DMF (2 mL). The reaction mixture was heated at 30° C. for 18 h, then partitioned between EtOAc and H2O, the aqueous layer washed with EtOAc, the organic layers combined, washed with brine, and dried (Na2SO4). Filtration and concentration to dryness gave the title compound after silica gel chromatography (0.1 to 0.2% CH3OH/NH4OH in CH2Cl2) and conversion to the hydrochloride salt.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in DMF (1 mL)
  3. temperatureThe reaction mixture was heated at 30° C. for 18 h
  4. custompartitioned between EtOAc and H2O
  5. washthe aqueous layer washed with EtOAc
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-256d2ec089464070aa37ed5f7c8c0bca
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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