Iodoethane → methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-1-ethyl-1H-benzimidazole-6-carboxylate

HRID 852659Notes

Reaction equation

HRID 852659 reaction equation
[O:1]=[S:2]1(=[O:21])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[C:16]2[N:15]=[CH:14][NH:13][C:12]=2[CH:11]=[C:10]([C:17]([O:19][CH3:20])=[O:18])[CH:9]=1.[H-].[Na+].[CH2:24](I)[CH3:25]>CN(C=O)C>[O:21]=[S:2]1(=[O:1])[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C:8]1[C:16]2[N:15]=[CH:14][N:13]([CH2:24][CH3:25])[C:12]=2[CH:11]=[C:10]([C:17]([O:19][CH3:20])=[O:18])[CH:9]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 69357660methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-1H-benzimidazole-6-carboxylate

Product 1

HCID 69358259methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-1-ethyl-1H-benzimidazole-6-carboxylateYield 160.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-1H-benzimidazole-6-carboxylate (D253) (230 mg, 0.74 mmol, 1 equiv) in DMF (10 ml) at room temperature was added NaH (60% dispersion in mineral oil, 33 mg, 0.82 mmol, 1.1 equiv) and the resulting mixture was stirred 5 min at this temperature. Ethyl iodide (66 μl, 0.82 mmol, 1.1 equiv) was added and the resulting solution was stirred for 30 min at 60° C. then cooled to room temperature and concentrated in vacuo. The residue was partitioned between AcOEt and a 5% aqueous citric acid solution. The two layers were separated and the aqueous phase saturated with NaCl and extracted twice with AcOEt. The combined organic phases were dried over MgSO4 and concentrated in vacuo to give methyl 4-(1,1-dioxidotetrahydro-2H-1,2-thiazin-2-yl)-1-ethyl-1H-benzimidazole-6-carboxylate (B151) (400 mg, 160%) as a pale yellow viscous oil which was used in the next step without further purification. [M+H]+=338.1, RT=2.43 min.

Workup

  1. stirringthe resulting solution was stirred for 30 min at 60° C.
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between AcOEt
  4. customThe two layers were separated
  5. extractionthe aqueous phase saturated with NaCl and extracted twice with AcOEt
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8689360c67b8485db499143ff90b84f9
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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