Methyl iodide → HCID 66934699, compound
Reaction equation
[C:1]([NH:4][C:5]1[CH:20]=[CH:19][C:8]([C:9]([NH:11][CH2:12][CH2:13][N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[O:10])=[C:7]([O:21][CH3:22])[CH:6]=1)(=[O:3])[CH3:2].[C:23](=O)([O-])[O-].[Cs+].[Cs+].[I:29]C>CN(C)C=O>[I-:29].[C:1]([NH:4][C:5]1[CH:20]=[CH:19][C:8]([C:9]([NH:11][CH2:12][CH2:13][N+:14]([CH2:15][CH3:16])([CH2:17][CH3:18])[CH3:23])=[O:10])=[C:7]([O:21][CH3:22])[CH:6]=1)(=[O:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
307 mg (1, mmol) of 4-acetylamino-N-(2-diethylamino-ethyl)-2-methoxy-benzamide is mixed in 8 ml of dimethylformamide with 358 mg (1.1 mmol) of cesium carbonate and 312 mg (2.2 mmol) of iodomethane, and it is heated under argon in a pressure vessel for 2.5 hours to a bath temperature of 80° C. After concentration by evaporation under vacuum, it is taken up in 25 ml of saturated sodium bicarbonate solution and extracted three times with 25 ml each of methylene chloride. The collected organic phase is dried, filtered and concentrated by evaporation, and 145 mg (32% of theory) of [2-(4-acetylamino-2-methoxy-benzoylamino)-ethyl]-diethyl-methyl-ammonium iodide with a melting point >300° C. is obtained.
Workup
- concentrationAfter concentration
- customby evaporation under vacuum, it
- extractionextracted three times with 25 ml each of methylene chloride
- customThe collected organic phase is dried
- filtrationfiltered
- concentrationconcentrated by evaporation, and 145 mg (32% of theory) of [2-(4-acetylamino-2-methoxy-benzoylamino)-ethyl]-diethyl-methyl-ammonium iodide with a melting point >300° C.
- customis obtained
Sources & evidence
- ORD record
- ord-b4cf512b24414ddb88ba1145d2c5719a
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07427390B2
Reaction notes
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