2-Mesitylenesulfonyl chloride → HCID 25066380, compound

HRID 1514853Notes

Reaction equation

HRID 1514853 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:12]=2[N:13]=1.CCN(C(C)C)C(C)C.[CH3:28][C:29]1[CH:34]=[C:33]([CH3:35])[CH:32]=[C:31]([CH3:36])[C:30]=1[S:37](Cl)(=[O:39])=[O:38]>O1CCOCC1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([NH:18][S:37]([C:30]3[C:31]([CH3:36])=[CH:32][C:33]([CH3:35])=[CH:34][C:29]=3[CH3:28])(=[O:39])=[O:38])[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

5

Reactant 3

HCID 130462-Mesitylenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 28370697HCID 28370697, compound

Product 1

HCID 25066380HCID 25066380, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a vial containing a solution of 2-(2,6-dichloro-phenyl)-3H-benzoimidazol-5-ylamine, prepared as described in Example 1-6, in dioxane (0.2 M, 0.10 mL) was added DIPEA (0.5 M in toluene, 0.050 mL), followed by 2,4,6-trimethyl-benzenesulfonyl chloride (0.2 M in toluene, 0.12 mL). After overnight at ambient temperature, solid phase extraction (SPE) by strong cation exchange (SCX) was followed by silica gel column chromatography to give N-[2-(2,6-Dichloro-phenyl)-3H-benzoimidazol-5-yl]-2,4,6-trimethyl-benzenesulfonamide: MS (m/z) 460.06 (M+1).

Workup

  1. customprepared
  2. extractionsolid phase extraction (SPE) by strong cation exchange (SCX)

Sources & evidence

ORD record
ord-92e45c9019d64bd181ce67b16dd9033c
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

Loading…