Methyl iodide → HCID 22890941, compound
Reaction equation
[CH3:1][O:2][P:3]([CH2:7][NH:8][S:9]([C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[CH:16]=1)(=[O:11])=[O:10])(=[O:6])[O:4][CH3:5].[C:21](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[CH3:1][O:2][P:3]([CH2:7][N:8]([S:9]([C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[CH:16]=1)(=[O:10])=[O:11])[CH3:21])(=[O:6])[O:4][CH3:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A reaction mixture consisting of 290 mg (0.83 mmol) of [(2-benzothiophenesulfonylamino)-methyl]-phosphonic acid dimethyl ester, 380 mg (1.16 mmol) of anhydrous cesium carbonate, 0.11 mL (1.16 mmol) of methyl iodide and 5 mL of anhydrous DMF stirred for 16 hours at room temperature. After the reaction was complete, DMF was evaporated in vacuum, and the residue was suspended in 15 mL of water and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate, filtered and evaporated, providing an oily residue which was chromatographed on a silica gel column, eluent EtOAc/hexane (7:3), then dichloromethane/MeOH (20:1), to yield the title compound as a yellowish oil (190 mg, 63%): 1H NMR: (300 MHz, CDCl3) δH 3.00 (s, CH3), 3.48 (d, J=11.5 Hz, 2 H), 3.83 (d, J=10.9 Hz, 6 H, 2CH3), 7.45-7.50 (m, 2 H, Ar—H), 7.83-7.89 (m, 3 H, Ar—H).
Workup
- customDMF was evaporated in vacuum
- extractionextracted with dichloromethane
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated
- customproviding an oily residue which
- customwas chromatographed on a silica gel column, eluent EtOAc/hexane (7:3)
Sources & evidence
- ORD record
- ord-e2b921e5388a4643a7a95bad00430e59
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06884791B2
Reaction notes
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