Dimethylformamide → HCID 58528853, compound

HRID 1431019Notes

Reaction equation

HRID 1431019 reaction equation
[I:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[C:14]([S:16][C:17]3[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=3)[CH:15]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[C:25]([O-])([O-])=O.[K+].[K+].IC.CN(C=O)C>CCOCC>[CH3:25][O:11][C:10](=[O:12])[C:9]1[CH:13]=[C:14]([S:16][C:17]2[N:18]([CH3:22])[CH:19]=[CH:20][N:21]=2)[CH:15]=[C:7]([O:6][C:5]2[CH:23]=[CH:24][C:2]([I:1])=[CH:3][CH:4]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58528803HCID 58528803, compound

Product 1

HCID 58528853HCID 58528853, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-(4-iodo-phenoxy)-5-(1-methyl-1H-imidazol-2-ylsulfanyl)-benzoic acid (1.4 g, 3.1 mmol), K2CO3 (856 mg, 6.2 mmol), iodomethane (0.29 mL, 4.65 mmol) and 16 mL of DMF were stirred for 2 h at rt. Then the mixture was diluted with ether and washed with water, brine, dried (MgSO4) and evaporated. The residue was adsorbed to SiO2 from CH2Cl2 and subjected to MPLC on a 40 g column of SiO2 eluting with % EtOAc in hexanes (time): 33% (10 min), 35-50% (20 min ramp) which provided 1.32 g (91%) of the title compound: 1H NMR (500 MHz, DMSO-d6): δ 3.63 (s, 3H), 3.79 (s, 3H), 6.91 (d, 21-1, J=8 Hz), 6.96 (dd, 1H, J=2, 1 Hz), 7.14 (d, 1H, J=1 Hz), 7.23 (dd, 1H, J=2, 1 Hz), 7.32 (t, 1H, J=1 Hz), 7.51 (d, 1H, J=1 Hz), 7.75 (d, 2H, J=8 Hz); LCMS (m/z): 467.4 [C18H15IN2O3S+H]+.

Workup

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-942b42eeafbe4af49116abd3af5f71c6
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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