Iodoethane → ethyl 3-(4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-6-yl)propionate

HRID 963100Notes

Reaction equation

HRID 963100 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH3:19])[S:17][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[CH:10]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[N:9]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:36][CH3:37].C(OCC)(=O)C>CN(C)C=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([CH2:18][CH3:19])[S:17][C:13]=2[N:12]2[C:20]([CH3:23])=[N:21][N:22]=[C:11]2[CH:10]([CH2:24][CH2:25][C:26]([O:28][CH2:36][CH3:37])=[O:27])[N:9]=1

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 677277213-(4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-6-yl)propionic acid

Product 1

HCID 67727690ethyl 3-(4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-6-yl)propionate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(4-(2-Chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-6-yl)propionic acid (13.5 g) was dissolved in dimethylformamide (140 ml). Potassium carbonate (9.1 g) and iodoethane (2.9 ml) were added, and the mixture was stirred for 4 hours. Ethyl acetate and water were added thereto. The organic layer was taken out, washed with brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was crystallized from diisopropyl ether to give 11.2 g of ethyl 3-(4-(2-chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-6-yl)propionate.

Workup

  1. washwashed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-f9e46504dcbb45dcb90834e96c0f69fe
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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